Reaction Steps
Aldehyde 22 and 2.5 eq sodium borohydride were reacted as in the preparation of 24 to give 47% alcohol 25 after chromatography (35 g SiO2, 2% EtOAc/1% TEA/97% CH2Cl2, Rf=0.34). 1H NMR (CDCl3, 360.134 MHZ δ:3.70 (1H, br d, J=11.02 Hz), 3.65 (1H,q,J=5.45 Hz), 3.46 (1H, br d), 2.85 (1H, br), 1.68 (1H,m), 1.46 (2H,m), 1.27 (2H,m), 092 (3H,d,J=5.45 Hz), 3.46 (1H, br d), 2.85 (1H, br), 1.68 (1H,m), 1.46 (2H,m), 1.27 (2H,m), 0.92 (3H,d,J=7.07 Hz), 0.90 (9H,t,J=7.90 Hz), 0.85 (3H,t,J=7.30 Hz), and 0.56 (6H,q,J=7.90 Hz). 13C NMR (CDCl3, 90.55 MHz) δ:77.6, 65.7, 38.0, 37.3, 18.0, 14.6, 14.3, 6.8, and 5.0. IR (thin film): 3400 (br) 2958(s), 2913(s), 2876(s), 1458(m), 1415(w), 1379(w), 1239(m), 1119(w), 1079(sJ), 1007 (s), 784 (w), 739 (s), and 727 (s) cm-1. High resolution MS (m/z): 217.1624, calcd for C11H25O2Si 217.1621 (M-C2H5).
