Pyridine → HCID 59779113, compound

Participants

Reaction Steps

A solution of 5-p-tolyl-bicyclo[3.1.0]hexan-2-ol (1 g, 5.3 mmol) in CH2Cl2 (20 mL) was treated with pyridine (0.6 mL, 7.4 mmol) followed by Dess-Martin periodinane (2.7 g, 6.3 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 (760 mg, 77%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.42-1.47 (m, 1 H) 1.53-1.61 (m, 1 H) 2.06-2.11 (m, 1 H) 2.20-2.29 (m, 2 H) 2.30-2.36 (m, 1 H) 2.32-2.34 (m, 3 H) 2.37-2.45 (m, 1 H) 7.08-7.18 (m, 4 H).

Provenance & Evidence