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With hydrogenchloride; ammonium chloride; In tetrahydrofuran; diethyl ether;
1-methylcyclohexane-1-carboxylic acid (10 g) in tetrahydrofuran was added dropwise to a stirred solution of lithium aluminium hydride (2.5 g) in tetrahydrofuran. After 1 h, saturated aqueous ammonium chloride then dilute hydrochloric acid were added, and the mixture was extracted with chloroform (x 3). The combined organic phase was dried (Na2SO4) and evaporated to yield the title alcohol as a colourless syrup (8 g), single component by g.c.-m.s. 4 Tetrahydrothiophene-2-methanol: the title alcohol was prepared from <strong>[19418-11-2]tetrahydrothiophene-2-carboxylic acid</strong> (J.T. Wrobel and E. Hejchman, Synthesis 1987, 452) by reduction with lithium aluminium hydride in ether (S. Ikegami, Tetrahedron 1974, 30 , 2087). 5 (RS)-2-Cyclohexene-1-methanol: cyclohexenone (10 g) was added dropwise to a solution of lithium aluminium hydride (2 g) in diethyl ether (50 ml) and the mixture was stirred at ambient temperature for 2 h. Saturated ammonium chloride solution (150 ml) was added, followed by hydrochloric acid (2 M) to dissolve the grey precipitate, and the mixture was extracted with chloroform (x 3), dried (MgSO4) and evaporated to a syrup. Fractional distillation under reduced pressure gave 2-cyclohexen-1-ol as a liquid, a single component by g.c.-m.s. The resulting 2-cyclohexen-1-ol (4 g) was converted to the title alcohol by the method of W. C. Still et al., (J. Am. Chem. Soc., 100 (1978) 1927-8, and after purification by flash crhomatography (silica; eluant ethyl acetate/light petroleum ether, 1:4) was obtained as a colourless liquid (2.5 g).
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