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molecular formula C16H17NO6 B031883 Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate CAS No. 88150-75-8

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

Número de catálogo B031883
Peso molecular: 319.31 g/mol
Clave InChI: RIGKLAOKQFKWNN-UHFFFAOYSA-N
Atención: Solo para uso de investigación. No para uso humano o veterinario.
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Patent
US04572909

Procedure details

Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10° while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10° a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.
Quantity
66.1 g
Type
reactant
Reaction Step One
Quantity
150 g
Type
reactant
Reaction Step One
Quantity
500 mL
Type
solvent
Reaction Step One
Quantity
129.3 g
Type
reactant
Reaction Step Two
Quantity
800 mL
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[H-].[Na+].[OH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].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>[C:10]1(=[O:11])[N:6]([CH2:5][CH2:4][O:3][CH2:18][C:19](=[O:26])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]12 |f:0.1|

Inputs

Step One
Name
Quantity
66.1 g
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
150 g
Type
reactant
Smiles
OCCN1C(C=2C(C1=O)=CC=CC2)=O
Name
Quantity
500 mL
Type
solvent
Smiles
O1CCCC1
Step Two
Name
Quantity
129.3 g
Type
reactant
Smiles
ClCC(CC(=O)OCC)=O
Step Three
Name
Quantity
800 mL
Type
reactant
Smiles
Cl
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
C(C)(=O)OCC
Step Four
Name
Quantity
0 (± 1) mol
Type
solvent
Smiles
O1CCCC1

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
stirring
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

ADDITION
Type
ADDITION
Details
was added
ADDITION
Type
ADDITION
Details
was added (750 ml)
WASH
Type
WASH
Details
The aqueous layer was washed with ethyl acetate (300 ml)
WASH
Type
WASH
Details
After washing with water (300 ml)
CUSTOM
Type
CUSTOM
Details
the ethyl acetate was evaporated

Outcomes

Product
Details
Reaction Time
18 h
Name
Type
product
Smiles
C1(C=2C(C(N1CCOCC(CC(=O)OCC)=O)=O)=CC=CC2)=O
Name
Type
product
Smiles
Measurements
Type Value Analysis
AMOUNT: MASS 243 g

Source

Source
Open Reaction Database (ORD)
Description
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.
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