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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

Cat. No. B031883
M. Wt: 319.31 g/mol
InChI Key: RIGKLAOKQFKWNN-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
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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.
Quantity
66.1 g
Type
reactant
Reaction Step One
Quantity
500 mL
Type
solvent
Reaction Step One
Quantity
150 g
Type
reactant
Reaction Step Two
Quantity
129 g
Type
reactant
Reaction Step Three
Quantity
250 mL
Type
solvent
Reaction Step Three
Quantity
800 mL
Type
reactant
Reaction Step Four
Quantity
750 mL
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[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|

Inputs

Step One
Name
Quantity
66.1 g
Type
reactant
Smiles
[H-].[Na+]
Name
Quantity
500 mL
Type
solvent
Smiles
O1CCCC1
Step Two
Name
Quantity
150 g
Type
reactant
Smiles
C1(C=2C(C(N1CCO)=O)=CC=CC2)=O
Step Three
Name
Quantity
129 g
Type
reactant
Smiles
ClCC(CC(=O)OCC)=O
Name
Quantity
250 mL
Type
solvent
Smiles
O1CCCC1
Step Four
Name
Quantity
800 mL
Type
reactant
Smiles
Cl
Name
Quantity
750 mL
Type
solvent
Smiles
C(C)(=O)OCC

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
The mixture was stirred at room temperature overnight
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
The organic phase was separated
CUSTOM
Type
CUSTOM
Details
the solvent was evaporated at reduced pressure
CUSTOM
Type
CUSTOM
Details
The residue separated into two layers
CUSTOM
Type
CUSTOM
Details
the upper layer of mineral oil was removed

Outcomes

Product
Details
Reaction Time
8 (± 8) h
Name
Type
product
Smiles
C(C)OC(CC(=O)COCCN1C(C=2C(C1=O)=CC=CC2)=O)=O
Measurements
Type Value Analysis
AMOUNT: MASS 243 g
YIELD: CALCULATEDPERCENTYIELD 97.1%

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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