[CH2:1]([Li])CCC.[C:6]([C:8]1([OH:23])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)#[CH:7].IC>CCCCCC.C1COCC1.CS(C)=O>[C:6]([C:8]1([O:23][CH3:1])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)#[CH:7]
28.85 ml of a 15% solution of butyllithium in hexane are added dropwise to a solution, cooled to −30° C., of 13.0 g of 4-ethynyl-4′-propylbicyclohexyl-4-ol in 24 ml of THF. A solution of 4.67 ml of iodomethane in 36 ml of dimethyl sulfoxide is subsequently added dropwise to the reaction mixture at −5° C. The mixture is stirred at RT overnight and subjected to conventional work-up, giving 4-ethynyl-4-methoxy-4′-propylbicyclohexyl (C 45 I, Δε−3.72, Δn−0.022).
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