Propargyl alcohol → 2-Decenol, (2E)-

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trans-2-Decen-1-ol was prepared by reduction of the propargyl alcohol by the method described by Jones and Denmark (Org. Syn., 1985, 64, 182-8) using 15 g (97 mmole) of 2-decyn-1-ol in 40 ml of ether and 48 ml (162 mmole) of Red-Al (sodium bis(2-methoxyethoxy)aluminum hybride) in 50 ml of ether. Kugelrohr distillation afforded 11.59 g of a clear oil. 1H NMR δ5.66 (m, 2), 4.07 (d, 2, J=5 Hz), 20.3 (dd, 2, J=6, 13 hz), 1.68 (br, 1), 1.4-1.2 (m, 10), 0.88 (t, 3, J=7 Hz).

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