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

HRID 246903ノート

反応式

HRID 246903 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77b12f613e3a4e96bf895fc158575c3d
出典データセット
uspto-grants-1987_11
特許番号
US04704462

反応ノート

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