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

HRID 29457

Reaction equation

HRID 29457 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 102411083-Methyl-2-benzofuranmethanolYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-5d8efb45f78b407db502724f69cc21b4
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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