Trifluoroacetic acid → {Bicyclo[4.1.0]heptan-1-yl}methanol

Participants

Reaction Steps

To a solution of diethyl zinc (1.0 M in hexanes, 15.70 mL, 15.70 mmol) in anhydrous dichloromethane (15.7 mL) was added dropwise trifluoroacetic acid (1.79 g in 15.7 mL anhydrous dichloromethane, 15.7 mmol) at 0° C. over 20 minutes. The reaction mixture was stirred at the same temperature for 20 minutes, and then added dropwise a solution of diidomethane (4.20 g, 15.70 mmol) in anhydrous dichloromethane (15.7 mL) at 0° C. over 10 minutes. The reaction mixture was further stirred at the same temperature for another 20 minutes. To this reaction mixture was added a solution of cyclohexenylmethanol (1.07 g, 6.30 mmol) in anhydrous dichloromethane (17 mL) at 0° C. The resulting mixture was warmed to ambient temperature and further stirred for 1 hour. The mixture was quenched with a saturated solution of ammonium chloride (50 mL) and separated the organic layer. The aqueous layer was extracted with dichloromethane (15 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to dryness. The residue was purified by column chromatography with diethyl ether in hexanes (30%) to afford the title compound as colorless oil (1.00 g, 86%): 1H NMR (300 MHz, CDCl3) δ 3.32 (dd, J=10.9, 10.9 Hz, 2H), 1.90-1.80 (m, 2H), 1.75-1.55 (m, 2H), 1.34 (br, s, 1H), 1.26-1.14 (m, 2H), 0.45 (dd, J=9.3, 4.5 Hz, 1H), 0.24 (t, J=4.9 Hz, 1H).

Provenance & Evidence