Synthesis of (8E,10Z)-Pentadecadien-1-ol Acetate
993
(dt, 1H, J1 ¼ 15 Hz, J2 ¼ 6 Hz), 5.93 (m, 1H), 6.23–6.39 (m, 1H). 13C NMR:
(CDCl3, 50 MHz) d: 13.66 (q), 19.37 (t), 22.00 (t), 25.23 (t), 25.90 (t), 27.09
(t), 28 86 (t), 29.05 (t), 29.44 (t), 30.48 (t), 31.61 (t), 32.56 (t), 61.95 (t), 67.32
(t), 98.48 (d), 125.31 (d), 128.30 (d), 129.67 (d), 132.22 (d). Mass (m/z): 308
(Mþ, 4), 290 (5), 252 (4), 224 (4), 163 (4), 149 (6), 135 (8), 121 (8), 110 (12),
95 (10), 85 (100), 67 (15), 55 (8).
(8E,10Z)-Pentadecadien-1ol acetate (1): A mixture of diene (12)
(225 mg, 0.72 mmol), acetyl chloride (87 mg, 1.08 mmol), and glacial acetic
acid (1.5 mL) was stirred overnight at room temperature. The reaction
mixture was poured on crushed ice and extracted with diethyl ether. The
organic layer was washed with aqueous sodium bicarbonate (5%, 5 mL),
water (5 mL), and brine (5 mL), dried over anhydrous Na2SO4, and concen-
trated in vacuum. Column chromatography on silica gel (eluent 5:95 ethyl
acetate–pet. ether) furnished the title compound. Yield: 180 mg (92%). IR
n
max: (CHCl3) cm21: 3010, 2954, 1730, 1215,756. 1H NMR: (CDCl3,
200 MHz) d: 0.91 (t, 3H, CH3, J ¼ 12 Hz, J ¼ 6 Hz), 1.28–1.36 (m, 12 H),
1.63 (m, 2H), 2.03 (s, 3H), 2.03–2.16 (m, 4H), 4.05 (t, 2H, –CH2–O–
COCH3, J ¼ 6 Hz), 5.29 (dt, 1H, J1 ¼ 12 Hz, J2 ¼ 6 Hz), 5.63 (dt, 1H,
J1 ¼ 15 Hz, J2 ¼ 6 Hz), 5.93 (m, 1H), 6.23–6.39 (m, 1H). 13C NMR:
(CDCl3, 50 MHz) d: 13.64 (q), 20.66 (q), 22.07 (t), 25.58 (t), 27.09 (t),
28.20 (t), 28.77 (t), 29.00 (t), 31.86 (t), 32.74 (t), 64.54 (t), 125.70 (d),
128.57 (d), 130.04 (d), 134.38 (d), 171.10 (s). Mass (m/z): 266 (M þ , 22),
206 (12), 177 (5), 163 (7), 149 (13), 136 (25), 121 (50), 109 (69), 95 (100),
81 (60), 67 (40).
ACKNOWLEDGMENT
R.K.K. and R.R.K. thank CSIR, New Delhi, India for senior research fellow-
ships. Funding from the Young Scientist Award, CSIR, New Delhi, India
is also gratefully acknowledged.
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