[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH2:12][OH:13])[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].[Br:16][C:17]1[S:18][C:19](C2C=CC=CC=2)=[N:20][N:21]=1>CN(C)C=O>[Br:16][C:17]1[S:18][C:19]([O:13][CH2:12][CH:9]2[CH2:8][CH2:7][CH:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[N:20][N:21]=14-Pentylcyclohexylcarbinol (1.5 g, 8.15 mmol) are dissolved in dimethylformamide (40 ml), and sodium hydride (0.3 g, 12.23 mmol) is added at room temperature over a period of about 15 minutes. When the gas evolution is complete, 2-bromo-5-phenyl-1,3,4-thiadiazole (2.95 g, 12.23 mmol) is added to the resultant alkoxide, and the mixture is subsequently stirred at 50° C. for 6 hours, poured onto an ice/water mixture, filtered with suction and extracted. Separation by column chromatography (SiO2, CH2Cl2) gives 1.2 g (43% of theory) of 2-bromo-5-(4-pentylcyclohexylmethoxy)-1,3,4-thiadiazole.
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