Hexane → HCID 19363547, compound

Participants

Reaction Steps

Combine methlytriphenylphosphonium bromide (3.08 g, 8.61 mmol) with THF (50 mL) and add a hexane solution of n-butyllithium (3.8 mL, 2.5 M, 9.47 mmol). After the addition is complete stir at ambient temperature for 0.5 hour. Add 4-(p-methoxybenzyloxy)-1-(t-butyldimethylsilyloxy)butan-2-one (2.65 g, 7.82 mmol) in THF (10 mL) and stir for 0.5 hours. Quench the reaction with saturated ammonium chloride solution and partition it between diethyl ether and water, wash the organic layer with water and then with saturated sodium chloride solution. Dry over MgSO4 and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/19 ethyl acetate/hexane to give the title compound as an oil. Rf =0.25; silica gel, 1/9 ethyl acetate/hexane. 1H NMR (CDCl3, 300 MHz) δ0.05 (s, 6H), 0.91 (s, 9H) 2.33 (t, J=6.98 Hz, 2H), 3.56 (t, J=6.98 Hz, 2H), 3.81 (s, 3H), 4.08 (s, 2H), 4.45 (s, 2H), 4.87 (s, 1H), 5.09 (d, J=1.65 Hz, 2H), 6.88 (d, J=8.73 Hz, 2H), 7.25 (d, J=8.73 Hz, 2H).

Provenance & Evidence