[CH:1]1([OH:5])[CH:3]([OH:4])[CH2:2]1.N1[CH:10]=[CH:9]N=C1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>CN(C=O)C.[Cl-].[Na+].O>[C:14]([Si:11]([CH3:13])([CH3:12])[O:5][C@H:1]1[CH2:10][CH2:9][C@H:3]([OH:4])[CH2:2]1)([CH3:17])([CH3:16])[CH3:15]To a stirred solution of 1,3-cyclopropanediol (5 g, 49 mmol) and imidazole (5 g, 73.4 mmol) in DMF (20 mL) was added t-butyldimethylsilyl chloride (5.2 g, 34.5 mmol) and the mixture was stirred for 90 minutes at room temperature. The mixture was diluted with brine (200 mL) and extracted with ether three times (1×100 mL and 2×50 mL). Each extract was washed with a portion of brine. The organic phases were combined, dried over sodium sulfate and evaporated to dryness. The mixture of cis/trans isomers was purified by column chromatography using ether and hexanes to give the predominant trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol as a colorless liquid (4.1 g).
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