Potassium Hydroxide → 4,4-Dimethyl-2-[4-(trifluoromethoxy)phenyl]-4,5-dihydro-1,3-oxazole
Reaction equation
O[CH2:2][C:3]([NH:6][C:7](=[O:19])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)([CH3:5])[CH3:4].S(Cl)(Cl)=O.[OH-].[K+]>>[CH3:5][C:3]1([CH3:4])[CH2:2][O:19][C:7]([C:8]2[CH:9]=[CH:10][C:11]([O:14][C:15]([F:16])([F:17])[F:18])=[CH:12][CH:13]=2)=[N:6]1Participants
4
Procedure
To a 25 ml round bottom flask was added N-(2-hydroxy-1,1-dimethylethyl)-4-(trifluoromethoxy)benzamide (4.2 g, 15.2 mmol). Thionyl chloride (3.32 ml, 45.5 mmol) was added. The resulting reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 100 g crushed ice. Solid KOH was added until the mixture became strongly basic. The mixture was extracted twice with 50 ml ethyl acetate. The extracts were dried over sodium sulfate, filtered and concentrated. The crude product was purified on silica gel column eluted with 1:10 ethyl acetate/hexane to give 2.6 g colorless liquid.
Workup
- customThe resulting reaction mixture
- additionThe reaction mixture was poured into 100 g
- customcrushed ice
- extractionThe mixture was extracted twice with 50 ml ethyl acetate
- dry with materialThe extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified on silica gel column
- washeluted with 1:10 ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-fddd4990920041f594d66552d8747a47
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304434B2
Reaction notes
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