Benzyl Alcohol → 3-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester

HRID 1628156ノート

反応式

HRID 1628156 の反応式
C(Cl)(=O)C(Cl)=O.[CH2:7]([C:14]1[CH:15]=[C:16]([CH2:21][CH:22]([O:26][CH2:27][CH3:28])[C:23]([OH:25])=[O:24])[CH:17]=[CH:18][C:19]=1[OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C=O)C.[CH2:34](O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:34]([O:24][C:23](=[O:25])[CH:22]([O:26][CH2:27][CH3:28])[CH2:21][C:16]1[CH:17]=[CH:18][C:19]([OH:20])=[C:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 6228DimethylformamideHCID 65578Oxalyl chloride2 回HCID 668649833-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid

生成物 1

HCID 668645693-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (0.364 g, 2.87 mmol) was added dropwise to a mixture of 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid (0.345 g, 1.15 mmol) and a catalytic amount of DMF in dry DCM (2.0 mL). The mixture was stirred for 17 h at room temperature before the excess oxalyl chloride was evaporated in vacuo. The remaining carboxylic acid chloride was redissolved in dry DCM (3.0 mL) and benzyl alcohol (0.15 g, 1.38 mmol) was added under nitrogen atmosphere. After stirring for 24 h at room temperature the solvent was removed in vacuo and the resulting oil was purified by column chromatography using DCM/MeOH (96:4) as the eluent to afford the title compound as an oil (0.22 g, 36.8%). Mass Spectrum: M−H+ 388.94.

後処理

  1. customwas evaporated in vacuo
  2. dissolutionThe remaining carboxylic acid chloride was redissolved in dry DCM (3.0 mL)
  3. customwas removed in vacuo
  4. customthe resulting oil was purified by column chromatography

出典と根拠

ORDレコード
ord-4d4e31c6a72b4d439a025ead4dda899e
出典データセット
uspto-grants-2014_07
特許番号
US08785681B2

反応ノート

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