[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][F:20].[H][H]>CO.N1C2C(=CC=CC=2)C=CC=1.[Pd]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][F:20]A solution of 12-fluoro-3-dodecyn-1-yl tetrahydropyranyl ether (0.5262 g, 1.85 mmol) (prepared as in Example 3 above) in methanol (10 mL) containing about 4 drops of quinoline is hydrogenated at room temperature over 5% palladium on barium sulfate (25 mg). The mixture is kept at about 762 psi of hydrogen until 41.5 ml (1.85 mmol) of hydrogen has been absorbed. The catalyst is then filtered off and the solvent removed in vacuo. The residue is purified by flash chromatography using hexane/ethyl acetate (9:1, v/v) to give 12-fluoro-(Z)-3-dodecen-1-yl tetrahydropyranyl ether (0.52 g, 99%) as a clear oil: Rf=0.65, hexane/ethyl acetate (7:3, v/v); IR (film) ν3025 (C=CH); and 1H-NMR δ1.20-1.80 (m, 18H), 2.05 (m,2H), 2.35 (br q, J=4 Hz, 2H), 3.60 (m, 4H), 4.41(dt, J=48 Hz, 2H), 4.56 (br s, 1H), 5.41 (m, 2H).
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