Lithium borohydride → trans-(2-(3-Chloro-2-methylphenyl)cyclopropyl)methanol

Participants

Reaction Steps

To a solution of trans-methyl 2-(3-chloro-2-methylphenyl)cyclopropanecarboxylate (0.042, 0.187 mmol) in THF (2.0 mL) was added 2.0 M lithium borohydride (0.467 ml, 0.935 mmol) dropwise at room temperature. The reaction was stirred at room temperature for 3 d. The mixture was partitioned between EtOAc and 1 N HCl. The organic layer separated, and the aqueous phase was extracted with EtOAc. The combined organic layer was dried (MgSO4) and concentrated to afford the title compound (23 mg, 63% yield) as pale-yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (d, J=8.0 Hz, 1H), 7.04 (t, J=7.7 Hz, 1H), 6.96 (d, J=8.0 Hz, 1H), 3.86-3.65 (m, 2H), 2.53-2.45 (m, 3H), 1.90-1.82 (m, 1H), 1.39 (d, J=5.2 Hz, 1H), 0.97-0.90 (m, 2H).

Provenance & Evidence