Pyridine → HCID 66781708, compound

Participants

Reaction Steps

A solution of 5-(3,4-dichlorophenyl)bicyclo[3.1.0]hexan-2-ol (455 mg, 1.88 mmol) in CH2Cl2 (10 mL) at 0° C. was treated with pyridine (0.38 mL, 4.6 mmol), followed by Dess-Martin periodinane (1.95 g, 4.6 mmol) and warmed to ambient temperature. After 2 h, 3 drops of H2O were added. After 0.5 h, the reaction was quenched with saturated NaHCO3, saturated Na2SO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried and concentrated in vacuo. Purification by silica gel chromatography gave the target compound (200 mg, 44%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.45-1.50 (m, 1 H) 1.51-1.58 (m, 1 H) 2.11 (dd, 1 H) 2.21-2.37 (m, 3 H) 2.37-2.45 (m, 1 H) 7.04 (dd, 1H) 7.32 (d, 1 H) 7.37 (d, 1 H).

Provenance & Evidence