Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
货号 B031883
分子量: 319.31 g/mol
InChI 键: RIGKLAOKQFKWNN-UHFFFAOYSA-N
注意: 仅供研究使用。不适用于人类或兽医用途。
Patent
US04661485
Procedure details
To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0° under nitrogen was added 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.
Identifiers
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REACTION_CXSMILES
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[H-].[Na+].[C:3]1(=[O:16])[N:7]([CH2:8][CH2:9][OH:10])[C:6](=[O:11])[C:5]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:4]12.Cl[CH2:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][C:19]([CH2:18][O:10][CH2:9][CH2:8][N:7]1[C:6](=[O:11])[C:5]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:4]2[C:3]1=[O:16])=[O:26])[CH3:25] |f:0.1|
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Inputs
Step One
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Name
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|
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Quantity
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66.1 g
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Type
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reactant
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Smiles
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[H-].[Na+]
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Name
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Quantity
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500 mL
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Type
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solvent
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Smiles
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O1CCCC1
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Step Two
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Name
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|
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Quantity
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150 g
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Type
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reactant
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Smiles
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C1(C=2C(C(N1CCO)=O)=CC=CC2)=O
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Step Three
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Name
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Quantity
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129 g
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Type
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reactant
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Smiles
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ClCC(CC(=O)OCC)=O
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Name
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|
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Quantity
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250 mL
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|
Type
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solvent
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Smiles
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O1CCCC1
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Step Four
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Name
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Quantity
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800 mL
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Type
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reactant
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Smiles
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Cl
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Name
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|
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Quantity
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750 mL
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Type
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solvent
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Smiles
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C(C)(=O)OCC
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Conditions
Temperature
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Control Type
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AMBIENT
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Stirring
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Type
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CUSTOM
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Details
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The mixture was stirred at room temperature overnight
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Rate
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UNSPECIFIED
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RPM
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0
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Other
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Conditions are dynamic
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1
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Details
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See reaction.notes.procedure_details.
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Workups
CUSTOM
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Type
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CUSTOM
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Details
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The organic phase was separated
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CUSTOM
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Type
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CUSTOM
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|
Details
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the solvent was evaporated at reduced pressure
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CUSTOM
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Type
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CUSTOM
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|
Details
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The residue separated into two layers
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CUSTOM
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Type
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CUSTOM
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|
Details
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the upper layer of mineral oil was removed
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Outcomes
Product
Details
Reaction Time |
8 (± 8) h |
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Name
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|
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Type
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product
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Smiles
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C(C)OC(CC(=O)COCCN1C(C=2C(C1=O)=CC=CC2)=O)=O
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Measurements
| Type | Value | Analysis |
|---|---|---|
| AMOUNT: MASS | 243 g | |
| YIELD: CALCULATEDPERCENTYIELD | 97.1% |
Source
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Source
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Open Reaction Database (ORD) |
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Description
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The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks. |
