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

HRID 1698356노트

반응식

HRID 1698356 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-52da24d321874a4fb2e4b5e5f5e49fea
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163773B2

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