3-Methyl-1-benzofuran-2-carboxylic acid → 3-Methyl-2-benzofuranmethanol

HRID 29457

반응식

HRID 29457 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:11](O)=[O:12].B.C1COCC1>C1COCC1.O>[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:11][OH:12]

참가 물질

5

반응물 2

HCID 6005913-Methyl-1-benzofuran-2-carboxylic acidHCID 2723981Borane;tetrahydrofuran

생성물 1

HCID 102411083-Methyl-2-benzofuranmethanol수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-methyl-benzofuran-2-carboxylic acid (2.0 g, 11.4 mmol, 1 eq) in 60 mL of THF under nitrogen was placed in water bath. Then 30 mL of BH3.THF (1.0 M in THF, 30 mmol, 2.6 eq) was added dropwise. The reaction mixture was allowed to stir at room temperature for 12 h. Then the reaction was quenched with methanol (10 mL). Solvent was removed in vacuo and the residue was subjected to column chromatography eluting with 20% ethyl acetate/hexane to give (3-methyl-benzofuran-2-yl)-methanol (1.6 g) in 87% yield. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.2 (s, 3 H) 4.5 (d, J=5.8 Hz, 2 H) 5.3 (t, J=5.8 Hz, 1 H) 7.3 (m, 2 H) 7.5 (m, 1 H) 7.6 (m, 1 H).

후처리

  1. customThen the reaction was quenched with methanol (10 mL)
  2. customSolvent was removed in vacuo
  3. washeluting with 20% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-5d8efb45f78b407db502724f69cc21b4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420001B2

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