3-Methyl-1-benzofuran-2-carboxylic acid → 3-Methyl-2-benzofuranmethanol
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
Product 1
Reagents, catalysts & solvents 2
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).