[CH3:1][C@H:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:3][CH2:4][CH2:5]O.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C.O>ClCCl>[CH3:13][S:14]([CH2:5][CH2:4][CH2:3][C@H:2]([CH3:1])[CH2:7][CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])(=[O:16])=[O:15]To a solution of 4-(R)-methyl-8-methylnon-7-enyl alcohol (3.25 g, 19.1 mmol) in dichloromethane (50 ml) at 0° C. was added methanesulfonyl chloride (2.29 g, 20.0 mmol) followed by triethylamine (3.04 g, 30.0 mmol). After stirring for 10 min at 0° C., the reaction was allowed to warm to 25° C. and stirred for 3 hr. The reaction was poured into water (50 ml), separated and washed with dichloromethane (50 ml). The organic portions were combined, dried (magnesium sulfate), and evaporated to give the 1-methanesulfonyl-4-(R)-methyl-8-methylnon-7-ene as a yellow oil which was used without further purification.
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