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

HRID 474329

반응식

HRID 474329 반응식
[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]

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f4b37a4b0eb74adbb5a5bd6de3382c84
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637526B2

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