Water → (2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-1-oxo-1H-inden-5-yl)trifluoromethanesulfonate
Reaction equation
[CH2:1]([C:5]1([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:13][C:12]2[C:7](=[C:8]([Cl:16])[C:9]([Cl:15])=[C:10]([OH:14])[CH:11]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].C([O-])([O-])=O.[K+].[K+].[F:29][C:30]([F:36])([F:35])[S:31](Cl)(=[O:33])=[O:32].O>CN(C)C=O>[CH2:1]([C:5]1([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:13][C:12]2[C:7](=[C:8]([Cl:16])[C:9]([Cl:15])=[C:10]([O:14][S:31]([C:30]([F:36])([F:35])[F:29])(=[O:33])=[O:32])[CH:11]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Racemic 2-butyl-6,7-dichloro-2-cyclopentyl-2,3-dihydro-5-hydroxy-1H-inden-1-one (34.1 g, 0.1M) was stirred in dimethylformamide (100 ml) with K2CO3 (41.5 g, 0.3M) at 25° for 20 minutes. The mixture was cooled to 15°, and trifluoromethanesulfonyl chloride (19.4 g, 0.115M) was added at 15°-20° over 20 minutes. The mixture was then stirred at 25° for 30 minutes and poured into a liter of ice and water. The oil was extracted with diethyl ether (4×125 ml) and the combined organic extracts were thoroughly washed with water, dried over (MgSO4) and concentrated under vacuum to obtain the product as a viscous amber oil weighing 47.3 g. This product was used in the next step without further purification.
Workup
- temperatureThe mixture was cooled to 15°
- extractionThe oil was extracted with diethyl ether (4×125 ml)
- washthe combined organic extracts were thoroughly washed with water
- dry with materialdried over (MgSO4)
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-674df01524d443f7b1c95ae2281adf2f
- Source dataset
- uspto-grants-1988_06
- Patent number
- US04754061
Reaction notes
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