[O:1]1[C:5]2[CH:6]=[C:7]([C:10](OC)=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>C1COCC1>[O:1]1[C:5]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1A solution of methyl 1-benzofuran-6-carboxylate (J. Med. Chem. 1995, 38, 3094; 142 mg, 0.8 mmol) in THF (5 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (92 mg, 2.4 mmol) in THF (2 mL) at −10° C. The mixture was stirred at room temperature for 30 min, cooled to 0° C. and treated slowly with water (1 mL). The mix was brought to pH 1 with 2N HCl and extracted with ethyl acetate (3×). The combined extracts were washed with water, brine, dried (MgSO4) and concentrated to give the final product.
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