3-Methoxy-5,5-dimethyl-7(E),9-decadien-1-o1

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Scheme

To a slurry of LAH (65 mg, 1.7 mmol) in ether (4 ml) at 0 ƒC under Ar, the diene ester [1] (487 mg, 1.7 mmol) in ether (5 ml) was added dropwise. After addition was complete, the reaction was quenched with sat aq Na₂SO₄. The solution was filtered and the solids were washed with ether (5 x 10 ml). The combined organic layers were dried over Na₂SO₄ and concentrated to give, after flash chromatography (1 : 1 pet ether : ether) the title alcohol as a colorless oil, 354 mg, in 97 percent yield.

¹H NMR (CDCl₃): d: 6.29 (dt, J = 16.9, 10.3Hz, 1H), 6.01 (dd, J = 15.3, 10.7Hz, 1H), 5.71 (dt, J = 15.3, 7.5Hz, 1H), 5.12 (d, J = 16.9Hz, 1H), 4.93 (d, J = 10.3Hz, 1H), 3.81 (m, 1H), 3.69 (m, 1H), 3.48 (m, 1H), 3.30 (s, 3H), 2.37 (bm, 2H), 1.99 (d, J = 7.6Hz, 2H), 1.88 (m, 1H), 1.60 (m, 2H), 1.28 (dd, J - 14.7, 4.0Hz, 1H), 0.90 (s, 3H), 0.88 (s, 3H).

IR (CH₂Cl₂): 3610, 3490, 2930, 1645, 1600, 1460, 1420, 1385, 1075, 1005, 895.

MS (m/e): 212 (M⁺, 8), 197, 180, 167, 143, 136, 124, 108, 89 (100).

1. Smith, D. tert-Butyl 3-methoxy-5,5-dimethyl-7(E),9-decadienoate Molecules 1997, 2, M34.

Sample Availability: No sample available.

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