Acetone → HCID 86755254, compound
Reaction equation
[CH3:1][C:2]([CH3:4])=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(C1C=CC(C=O)=CC=1[NH:26][C:27](=[O:45])[CH2:28][CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]([F:44])([F:43])[F:42])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])(C)(C)C.[C:46]([O:49]CC)(=[O:48])[CH3:47].C[CH2:53][CH2:54][CH2:55][CH2:56][CH3:57].[CH3:58]C(C)=O>>[C:2]([C:55]1[CH:54]=[CH:53][C:47]([C:46]([OH:49])=[O:48])=[CH:57][C:56]=1[CH:28]([CH:29]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41]([F:43])([F:44])[F:42])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:27]([NH2:26])=[O:45])([CH3:4])([CH3:58])[CH3:1]Participants
5
Procedure
1.2 ml of 1.6 M Jones' reagent were added to a solution of 426 mg (1.0 mmol) of N-(2-t-butyl-5-formylphenyl)-3-(2-trifluoromethylphenyl)octanamide (prepared as described in Preparation 20) in 8 ml of acetone, whilst ice-cooling, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was washed three times with water and then once with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by istillation under reduced pressure, to give 396 mg (yield 90%) of the title compound as crystals, melting at 199-200° C. (from ethyl acetate-hexane).
Workup
- temperaturecooling
- washAt the end of this time, the reaction mixture was washed three times with water
- dry with materialonce with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate
- customThe solvent was removed by istillation under reduced pressure
Sources & evidence
- ORD record
- ord-ca0993297e14429a925627bacfbd2a3b
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06040339
Reaction notes
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