[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:1]([O:8][CH:9]1[CH2:13][CH2:12][CH:11]([O:14][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
To a solution of 3-(tert-butyldimethylsilanyloxy)cyclopentanol (3.5 g, 16 mmol) in DCM (30 mL) was added triethylamine (2.65 mL, 19.4 mmol) and DMAP (20 mg, 0.16 mmol). The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (1.34 mL, 16.5 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 16 h. The reaction mixture was washed with water and the organic layer was dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (20% diethyl ether:hexanes) afforded 2.5 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 5.19-5.3 (m, 1H), 4.4 (m, 1H), 3.0 (s, 3H), 1.8-2.3 (m, 4H), 1.5-1.7 (m, 2H), 0.86 (s, 9H), 0.05 (s, 6H).
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