Dimethylformamide dimethyl acetal → Ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylate

HRID 1466551Notes

Reaction equation

HRID 1466551 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([CH:7]=1)[C:8]([C:9](=[CH:20][N:21]([CH3:23])[CH3:22])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

Product 1

HCID 66847508Ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylateYield 80%

Conditions

Temperature
90 °C

Procedure

A stirred mixture of ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate (10.02 mmol, 1 eq) and 1,1-dimethoxy-N,N-dimethylmethanamine (3.0 mL, 22 mmol, 2.2 eq) was heated at 90° C. for 2 hours. After evaporation of excess 1,1-dimethoxy-N,N-dimethylmethanamine, the crude product was purified by flash chromatography on silica gel (0 to 80% ethyl acetate in dichloromethane) to yield 2.493 g (80%) of ethyl 2-(5-chloro-2-methoxybenzoyl)-3-(dimethylamino)acrylate. LCMS (ESI) m+H=312.2.

Workup

  1. customAfter evaporation of excess 1,1-dimethoxy-N,N-dimethylmethanamine
  2. customthe crude product was purified by flash chromatography on silica gel (0 to 80% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-cd1130701c034ea5b7ad4e93f912fb04
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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