Reaction Steps
The alcohol 7 (6 g, 29.37 mmol), prepared according to Example 6, was oxidized using 2M (COCl)2 (18 mL, 36 mmol), dry DMSO (5.1 mL, 72 mmol) and triethyl amine (20.7 mL, 144 mmol) analogous to the oxidation of the alcohol 4, as described in example 4. Similar work up as for 5 gave the aldehyde 8 (4.8 g, 81%) as a colorless oil. IR (KBr) υmax 2939, 2880, 2735, 1719, 1451, 1391, 1111, 1038, 947 cm−1: 1HNMR (CDCl3) δ1.45-2.85 (m, 5 H), 2.54 (t, J=6.8 Hz, 2 H), 3.31 (s, 3 H), 3.43-3.46 (m, 2 H), 3.83-3.95 (m, 4 H), 2.54 (t, J=6.8 Hz, 2 H), 3.31 (s, 3 H), 3.43-3.46 (m, 2 H), 3.83-3.95 (M, 4 H), 4.77 (d, J=3.3 Hz, 1 H), 9.76 (t, J=1.5 Hz, 1 H); 13CNMR (CDCl3) δ21.51, 29.23, 37.99, 41.72, 58.42, 64.81, 64.88, 70.66, 106.26, 202.39: mass spectrum (EI), m/z (rel intensity) 210 (33), 202 (M+, 3), 201 (15), 157 (19), 144 (27), 143 (38), 141 (19), 127 (17), 126 (1), 111 (30), 109 (12), 100 (4), 99 (11), 73 (100), 59 (10), 57 (8), 55 (12), 54 (5).
