61826-40-2

5685-38-1

61826-40-2

Step 1: Sodium borohydride (567 mg, 15 mmol) was added in batches to a stirred solution of cooled 2-phenylcyclopropanecarboxylic acid (1.62 g, 10 mmol) in tetrahydrofuran (THF, 80 ml) at 0°C. Subsequently, boron trifluoride ethyl ether complex (2.13 g, 15 mmol) was slowly added dropwise to the reaction system. The reaction mixture was stirred continuously at 0°C for 1 hour, followed by raising to room temperature and stirring overnight. After completion of the reaction, the reaction mixture was carefully diluted with deionized water and extracted with ethyl acetate (EtOAc, 200 ml). The organic phase was washed sequentially with deionized water (70 ml) and saturated saline (80 ml). The organic layer was collected, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure to give the colorless oily product (1), trans-2-phenyl-1-cyclopropylmethanol, in a yield of 1.49 g (100% yield). The product was detected by infrared spectroscopy (IR, pure) with characteristic absorption peaks of 3350, 1605, 1490, 1090, 1035, 1020, and 695 cm-1. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR, CDCl3) showed δ 7.05-7.29 (m, 5H, arylhydrogen), 3.62 (d, J = 7Hz, 2H, CH2OH), and 2.28 (br s, 1H, OH), 1.81 (m, 1H, cyclopropane hydrogen), 1.46 (m, 1H, cyclopropane hydrogen), and 0.95 (m, 2H, cyclopropane hydrogen).