Fluoride Ion → HCID 9795641、化合物
反応式
[C:1]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C)C)=[CH:15][C:14]=2[O:27][Si](C(C)(C)C)(C)C)[CH2:9][CH2:8]1)(=[O:4])[CH2:2][CH3:3].[F-]>CO>[C:1]([O:5][CH2:6][CH:7]1[CH2:8][CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[OH:27])[CH2:11][CH2:12]1)(=[O:4])[CH2:2][CH3:3]参加物
4
実験手順
A mixture of [4-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methyl propionate (110 mg), methanol (10 ml) and Amberlyst fluoride resin (0.4 g) were stirred at room temperature for 72 hr. The reaction mixture was filtered, and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:2 v/v) to give the title compound as a cream solid and a mixture of diastereoisomers (44 mg, 73%). δH (CDCl3) 1.17 (3H, t), 1.38-2.14 (9H, m), 2.34-2.40 (2H, q), 2.64-2.80 (1H, m), 3.96 (0.6H, d), 4.20 (0.4H, d), 5.10-5.24 (2H, m), 6.28-6.33 (1H, m), 6.36-6.40 (1H, m), 6.98 (1H, dd); m/z (ES+) 279 (M+H)+.