4404
J. Org. Chem. 1992,57,4404-4414
times. The extracts were washed with brine, dried, and evarporated to give a crude aldehyde (12). To a suspension of methyltriphenylphcephonium bromide (161 mg,0.452 m o ) in THF (600pL) was added 1M lithium bis(trimethylsily1)amide in THF (434 p L , 0.434 mmol) at -20 OC. After being stirred for 15 min, the mixture was gradually warmed to rwm temperature. After being stirred for 15 min, the mixture was cooled to -20 OC, and a solution of 12 (0.328 "01) in THF (360 pL) was added. The reaction mixture was warmed to room temperature, stirred for 2 h, and quenched with saturated NH,Cl. The mixture was extracted with ether three times. The extracts were washed with brine, dried, and evaporated to give an oil, which was chromatographed on alumina to yield 2 (47 mg, 58%) as an oil: bp 75 +11.3' (c 2.255, CHCI,); IR OC/0.4 mmHg (Kugelrohr); (neat) 2925, 2855 cm-'; 'H NMR (CDCl,) 6 1.10 (3 H, d, J = 6.4 Hz), 1.29-1.63 (16 H, m), 1.88-2.02 (6 H, m), 2.56-2.67 (1H, m), 2.71-2.83 (1H, m), 3.54-3.65 (1H, m), 4.89-5.03 (2 H, m), 5.72-5.89
(1 H, m); I3C NMR (CDCl,) 6 22.00 (CH,), 27.27 (CH,), 28.97 (CH,), 29.14 (CHt), 29.55 (CH,), 29.89 (CHa, 31.76 (CH,), 32.14 (CHZ), 32.45 (CH,), 33.84 (CHJ, 34.50 (CHa,37.18 (CHJ, 61.71 (CH),64.99 (CH), 66.64 (CH), 114.12 (
