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
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
11.70 g (35.19 mmol) of tert-butyl [4-(acetoxymethyl)phenyl](cyclopentyl)acetate were dissolved in 108.5 ml of dichloromethane, the mixture was cooled to 0° C. and 39.2 ml of trifluoroacetic acid were added. The reaction mixture was stirred first at 0° C. for 1.5 h and then at RT for 1.5 h and then concentrated under reduced pressure. The residue was taken up in 50 ml of dichloromethane and the solution was washed four times with in each case 30 ml of water. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure and the residue was dried under high vacuum. This gave 9.83 g of the target compound as a crude product (about 90% pure, yield 91% of theory).
Workup
- waitat RT for 1.5 h
- concentrationconcentrated under reduced pressure
- washthe solution was washed four times with in each case 30 ml of water
- dry with materialThe organic phase was dried over magnesium sulphate
- concentrationconcentrated under reduced pressure
- customthe residue was dried under high vacuum
Sources & evidence
- ORD record
- ord-a6fd8cf477c248f08935d033f318fe38
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018258B2
Reaction notes
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