(2E,13Z)-2,13-Octadecadienyl Acetate
923
was dissolved in THF (0.8mL) and slowly added to the stirred and cooled
(276 8C) freshly prepared solution of the n-pentylidenetriphenylphosphorane
[prepared by addition a solution of sodium bis(trimethylsilyl)amide (0.41 g,
2.2 mmol) in THF (2mL) to suspension of n-pentyl-triphenylphosphonium
bromide (0.83g, 2 mmol) in THF (3mL) and heating under reflux for 40 min].
Afterthe addition, the reactionmixture wasstirredfor 1 h atthesametemperature
and then left overnight at room temperature. Removal of the solvent furnished a
residue, which was diluted with the mixture of hexane–ether 1:1 (10 mL),
washed with water (5 mL), and dried over MgSO4. A subsequent evaporation
of the solvent and flash chromatography (eluent: hexane–ether 7:1) afforded
170 mg (30% yield from 6) of the pure target compound, acetate 1. IR: 1747
1
(C55O), 1024 (C–O), 968 (HC55CH) trans, 720 (HC55CH) cis; H NMR:
0.89 (t, 3H, J ¼ 7.0, CH3), 1.20–1.46 (m, 18H, 9CH2), 1.95–2.16 (m, 6H,
3CH2CH55C), 2.06 (s, 3H, COCH3), 4.50 (dd, 2H, J ¼ 0.9, 6.3, CH2OAc),
5.35 (m, 2H, J ¼ 4.6, 11.0, CH55CH), 5.57 (dtt, 1H, J ¼ 1.2, 6.4, 15.3,
CH55C), 5.75 (dt, 1H, J ¼ 6.5, 15.3, CH55C); HRMS (ESI): [M þ Na]þ m/e
331.2623, calcd. for C20H36O2Na 331.2608. The spectral properties of 1 are in
excellent agreement with those previously described.[4–8]
REFERENCES
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232372m; (b) Sorochinskaya, A. M.; Kovalev, B. G. Synthesis of trans-2, cis-13- and
trans-3, cis-13- octadecadien-1-ol, components of the sex pheromone of Synanthedon