[O:1]1[CH2:3][C@H:2]1[CH2:4][OH:5].N1C=CN=C1.[C:11]([Si:15](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH3:14])([CH3:13])[CH3:12]>ClCCl>[C:11]([Si:15]([O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([CH3:14])([CH3:12])[CH3:13]To an ice-chilled mixture of (2R)-oxiran-2-ylmethanol (2.00 g, 27.0 mmol) and imidazole (3.68 g, 54.0 mmol) in anhydrous dichloromethane (60 mL) was added tert-butyl(chloro)diphenylsilane (8.40 mL, 32.4 mmol) dropwise, causing the formation of a white precipitate. The mixture was stirred at 0° C. for 15 minutes, then the cooling bath removed and stirring continued at room temperature for one hour. Aqueous ammonium chloride solution (2M, 100 mL) was added and the layers separated. The aqueous layer was extracted with dichloromethane (100 mL). The combined organic extracts were dried over sodium sulfate, concentrated, and purified by silica gel chromatography (eluting with a gradient of 0-30% ethyl acetate in heptane), affording tert-butyl[(2S)-oxiran-2-ylmethoxy]diphenylsilane (296h, 8.40 g, 99% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ 7.65-7.76 (m, 4H), 7.36-7.49 (m, 6H), 3.88 (dd, J=11.86, 3.30 Hz, 1H), 3.74 (dd, J=11.80, 4.71 Hz, 1H), 3.10-3.20 (m, 1H), 2.76 (dd, J=5.14, 4.16 Hz, 1H), 2.63 (dd, J=5.14, 2.69 Hz, 1H), 1.09 (s, 9H). MS: 330 [M+1].
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