Reaction Steps
The alcohol (15 (16.8 g, 59.92 mmol), prepared according to Example 13, was oxidized using 2 M (COCl)2 (37.50 mL, 75 mmol), dry DMSO (10.6 mL, 150 mmol), and triethylamine (43 mL, 300 mmol) as for the oxidation of compound 12. Similar work up as for 13 gave a crude product, which was purified by column chromatography eluting with ether/hexane (2:1), to give the aldehyde 16 (4.8 g, 81%) as a colorless oil. IR (KBr)νmax 29.42, 2878, 2725, 1723, 1496, 1434, 1413, 1368, 1211, 1153, 1098, 1031, 951, 742, 661 cm−1; 1HNMR (CDCl3)δ 1.56-1.86 (m, 5 H), 2.52 (t, J=7.6 Hz, 2H), 3.52-3.57 (m, 2H), 3.79-3.92 (m, 4 H), 4.48 (s, 2 H), 4.75 (d, J=3.3 Hz, 1 H), 7.25-7.34 (m, 5 H), 9.71 (s, 1 H); 13CNMR (CDCl3)δ 21.48, 29.33, 38.00, 41.71, 64.79, 68.73, 72.82, 106.28, 127.42, 127.55, 128.55, 128.25, 138.48; mass spectrum (EI), m/z (rel intensity) 279 (M+−1.7.5), 219(7), 171 (15), 144(8), 127(53), 91(31), 83(9), 73(100), 65(4).
