Water → [3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

HRID 1698356ノート

反応式

HRID 1698356 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=[C:6]([O:16][CH3:17])[CH:5]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[CH3:17][O:16][C:6]1[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([O:10][CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:7]=1

参加物

5

反応物 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59817706Methyl 3-methoxy-5-(3-methoxypropoxy)benzoate

生成物 1

HCID 59817758[3-Methoxy-5-(3-methoxypropoxy)phenyl]methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A mixture of 3-Methoxy-5-(3-methoxy-propoxy)-benzoic acid methyl ester (5 g, 19.7 mmol) and LAH (528 mg, 20 mmol) in THF (110 mL) is stirred under N2 at 0° C. for 3 h. After adding H2O, the reaction mixture is extracted with EtOAc. The combined organic phases are washed with H2O, brine and dried (Na2SO4). Concentration under reduced pressure and silica gel flash chromatography give the title compound as colorless oil. MS: 227 [M+H]+; tR (HPLC, CombiScreen ODS-AM 50×4.6 mm; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 5 min then 100% CH3CN+0.1% TFA for 2 min, flow 2.0 ml/min): 2.85 min.

後処理

  1. extractionthe reaction mixture is extracted with EtOAc
  2. washThe combined organic phases are washed with H2O, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration under reduced pressure and silica gel flash chromatography

出典と根拠

ORDレコード
ord-52da24d321874a4fb2e4b5e5f5e49fea
出典データセット
uspto-grants-2012_04
特許番号
US08163773B2

反応ノート

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