Diisopropylamine → 2-(3-Chloro-2,4,5-trifluorophenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole
Reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[C:22]1[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=1.[Cl:29]C(Cl)(Cl)C(C(Cl)(Cl)Cl)=O>C1COCC1.O>[Cl:29][C:19]1[C:14]([F:13])=[C:15]([C:22]2[O:23][CH2:24][C:25]([CH3:28])([CH3:27])[N:26]=2)[CH:16]=[C:17]([F:21])[C:18]=1[F:20]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 7.6 ml (54.2 mmol) of diisopropylamine in 100 ml of dry THF was cooled to -78° C. under argon, treated with 20.5 ml (47.2 mmol) of 2.3M n-butyllithium, and stirred for 15 minutes. To this solution was added a solution of 10.3 g (45.0 mmol) of 2-(2,4,5-trifluorophenyl)-4,4-dimethyl-2-oxazoline in 100 ml of dry THF. The reaction mixture was stirred at -78° C. for 45 minutes. To this mixture was added 26.5 g (100 mmol) of hexachloroacetone, and the solution was warmed to room temperature. Water was added; the organic phase was washed with water, 1N hydrochloric acid, and 5% sodium bicarbonate, and was dried over magnesium sulfate. Concentration gave a dark oil which was chromatographed on silica gel to give 7.05 g of the title compound as a yellow oil.
Workup
- stirringThe reaction mixture was stirred at -78° C. for 45 minutes
- washthe organic phase was washed with water, 1N hydrochloric acid, and 5% sodium bicarbonate
- dry with materialwas dried over magnesium sulfate
- concentrationConcentration
- customgave a dark oil which
- customwas chromatographed on silica gel
Sources & evidence
- ORD record
- ord-ca944cf943e94d97bbbbde4086bfbda2
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04920120
Reaction notes
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