Water → Ethyl 4-(2-tert-butoxycarbonylcyclopropyl)-2,3,5trifluorobenzoate
Reaction equation
[C:1]([CH:4]1[CH2:6][CH:5]1[C:7]1[C:17]([F:18])=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([F:19])[C:8]=1[F:20])([OH:3])=[O:2].Cl(O)(=O)(=O)=O.C(OCC)(=O)C.O.C(O[C:37]([CH3:40])([CH3:39])[CH3:38])(=O)C>>[C:37]([O:2][C:1]([CH:4]1[CH2:6][CH:5]1[C:7]1[C:17]([F:18])=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:9]([F:19])[C:8]=1[F:20])=[O:3])([CH3:40])([CH3:39])[CH3:38]Participants
Procedure
In 10 ml of tert-butyl acetate was dissolved 1.00 g of ethyl 4-(2-carboxycyclopropyl)-2,3,5-trifluorobenzoate. To the resulting solution was added 0.2 ml of a 70% aqueous perchloric acid solution. The resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture were added 40 ml of ethyl acetate and 20 ml of water in this order. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was purified by a column chromatography (eluant: n-hexane/toluene=1/1) to obtain 0.81 g (yield: 68.1%) of ethyl 4-(2-tert-butoxycarbonylcyclopropyl)-2,3,5trifluorobenzoate.
Workup
- customThe organic layer was separated
- washwashed with water
- dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
- customThe solvent was removed by distillation under reduced pressure
- customThe residue obtained
- customwas purified by a column chromatography (eluant: n-hexane/toluene=1/1)
Sources & evidence
- ORD record
- ord-60dba68a860c4ecfb5e5e18c6ab3ac03
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04990508
Reaction notes
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