[CH:1]1([CH2:4][C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=2)[C:8](OC)=[O:9])[CH2:3][CH2:2]1.[BH4-].[Li+]>C1COCC1>[CH:1]1([CH2:4][C:5]2[CH:6]=[C:7]([CH2:8][OH:9])[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3]1To a solution of methyl 3-(cyclopropylmethyl)benzoate (9.06 g, 47.6 mmol) in THF (100 mL) was added lithium borohydride (2.0 M in THF, 71.4 mL, 142.9 mmol). After stirring at 50° C. for 1 h the reaction was cooled, quenched with excess methanol and concentrated under vacuum. Purification by silica gel chromatography (30% EtOAc/hexanes) afforded the desired product.
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