Veratraldehyde → Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

HRID 246903노트

반응식

HRID 246903 반응식
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=O>ClCCl>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[CH:31]=[CH:6][C:1]([O:3][CH2:4][CH3:5])=[O:2]

참가 물질

4

반응물 2

HCID 8419VeratraldehydeHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester

생성물 1

HCID 2794876Ethyl 3-(3,4-dimethoxyphenyl)prop-2-enoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Carbethoxymethylene triphenylphosphorane (150 g, 0.3 mol) was added to a solution of 3,4-dimethoxybenzaldehyde (50 g, 0.3 mol) in dry dichloromethane (150 ml), and the mixture was stirred at room temperature overnight. The solution was concentrated to about 50 ml, and the precipitate was filtered off and washed with hexane-dichloromethane (4:1, v/v). The combined filtrates were evaporated to a residue, which was purified by silica gel chromatography using hexane-ethyl acetate (9:1, v/v) as the eluant. The title compound was isolated as a crystalline mass (65 g, 91%), m.p. 52°-53° C.

후처리

  1. concentrationThe solution was concentrated to about 50 ml
  2. filtrationthe precipitate was filtered off
  3. washwashed with hexane-dichloromethane (4:1
  4. customThe combined filtrates were evaporated to a residue, which
  5. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-77b12f613e3a4e96bf895fc158575c3d
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04704462

반응 노트

불러오는 중…