Trifluoroacetic acid → [4-(Acetoxymethyl)phenyl](cyclopentyl)acetic acid
Reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:13]([O:15]C(C)(C)C)=[O:14])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C:13]([OH:15])=[O:14])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
13.27 g (37.2 mmol, 95% pure) of tert-butyl(+/−)-{4-[(acetyloxy)methyl]phenyl}(cyclopentyl)acetate were dissolved in 117 ml of dichloromethane, the mixture was cooled to 0° C. and 58.4 ml of trifluoroacetic acid were added. The reaction mixture was initially stirred at 0° C. for 1.5 h and then at RT for a further 1.5 h. The mixture was then concentrated under reduced pressure and the residue was dried under high vacuum. The residue was taken up in 50 ml of dichloromethane, and the solution was washed four times with water. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. Drying under high vacuum gave 11.41 g of the title compound which were used without further purification for the next reaction.
Workup
- waitat RT for a further 1.5 h
- concentrationThe mixture was then concentrated under reduced pressure
- customthe residue was dried under high vacuum
- washthe solution was washed four times with water
- dry with materialThe organic phase was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customDrying under high vacuum
Sources & evidence
- ORD record
- ord-85362638eb3d43feafcd2d3360908f10
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08987256B2
Reaction notes
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