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

HRID 29457

反応式

HRID 29457 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 102411083-Methyl-2-benzofuranmethanol収率 87%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-5d8efb45f78b407db502724f69cc21b4
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

関連ノート

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