[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[CH:8])=[CH:3][CH:2]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1CCCC1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:11]2[CH:16]=[CH:15][C:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)=[CH:3][CH:2]=125.0 g of p-tolylacetylene and 12.71 g of tetrakis(triphenylphosphine)palladium(0) (9.2% of Pd) were introduced into 500 ml of pyrrolidine, and 65.36 g of [4-(4-bromophenyl)cyclohexyl]methanol were added quickly. The mixture was then warmed at 80° C. for 2.5 hours with stirring, cooled and subjected to conventional work-up, giving [4-(4-p-tolylethynylphenyl)cyclohexyl]methanol as a crystalline solid.
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