Trifluoroacetic acid → [4-(Bromomethyl)phenyl](cyclopentyl)acetic acid

반응식

FC(F)(F)C(O)=O.C([O:12][C:13](=[O:28])[CH:14]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][Br:27])=[CH:22][CH:21]=1)[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)(C)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([CH:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:13]([OH:28])=[O:12])=[CH:21][CH:22]=1

참가 물질

실험 절차

1.635 ml (2.420 g, 21.228 mmol) of trifluoroacetic acid were added to a solution of 500 mg (1.415 mmol) of tert-butyl[4-(bromomethyl)phenyl](cyclopentyl)acetate (Example 10A) in 5 ml of dichloromethane. The mixture was stirred at room temperature for 2 h. Saturated aqueous sodium bicarbonate solution was then added, and the mixture was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated under reduced pressure. This gave 364 mg (87% of theory) of the title compound.