Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate

HRID 1690607ノート

反応式

HRID 1690607 の反応式
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15].[CH2:16]([O:18][C:19]([CH:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:20])[CH3:17]>O1CCCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:21][C:19]([O:18][CH2:16][CH3:17])=[O:20])=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15]

参加物

4

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 866332964-Hydroxy-3-(3-methoxypropoxy)benzaldehyde

生成物 1

HCID 66907011Ethyl 3-[4-hydroxy-3-(3-methoxypropoxy)phenyl]acrylate収率 80.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4-hydroxy-3-(3-methoxypropoxy)benzaldehyde (15 g, 71.3 mmol) was dissolved in tetrahydrofuran (142 mL) and (ethoxycarbonylmethylene)triphenylphosphorane (24.8 g, 71.3 mmol) was added at room temperature portionwise. The mixture was then stirred overnight. The solvents were evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2) to yield 16 g (80%) of the desired product as a yellow oil of a mixture of E and Z isomers.

後処理

  1. customThe solvents were evaporated under reduced pressure
  2. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 8/2)
  3. customto yield

出典と根拠

ORDレコード
ord-b9bb2d5107014abca499a34c8e4b323a
出典データセット
uspto-grants-2012_04
特許番号
US08153647B2

反応ノート

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