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

HRID 474329

Reaction equation

HRID 474329 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=1.CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:7]=1)[C:8]([C:9](=[CH:19][N:20]([CH3:22])[CH3:21])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58063452Ethyl 3-(5-chloro-2-methylphenyl)-3-oxopropanoate

Product 1

HCID 66677099Ethyl 2-(5-chloro-2-methylbenzoyl)-3-(dimethylamino)acrylateYield 34.2%

Procedure

A solution of ethyl 3-(5-chloro-2-methylphenyl)-3-oxopropanoate (28.4 mmol) in 1,1-dimethoxy-N,N-dimethylmethanamine (10.0 mL, 75.3 mmol, 2.6 equiv) was heated at 90° C. After 3 hours, the reaction mixture was concentrated in vacuo, and the resultant residue was purified by flash column chromatography on silica gel (0 to 80% ethyl acetate in dichloromethane) to yield 2.87 g (34%) of ethyl 2-(5-chloro-2-methylbenzoyl)-3-(dimethylamino)acrylate. LCMS (ESI) m+H=296.3.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customthe resultant residue was purified by flash column chromatography on silica gel (0 to 80% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-f4b37a4b0eb74adbb5a5bd6de3382c84
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Linked notes

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