Fluoride Ion → HCID 9795641, compound
Reaction equation
[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]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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)+.