Bicarbonate Ion → 5-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde
Reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][OH:13])[C:8]=2[C:14]([F:17])([F:16])[F:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-]>ClCCl>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]=[O:13])[C:8]=2[C:14]([F:16])([F:17])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of (5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)methanol (step A, 1.79 g, 7.36 mmol) in dichloromethane (23 mL) at 0° C. was added Dess-Martin Periodinane (3.43 g, 8.10 mmol). The reaction mixture was stirred at 0° C. for 10 min. and then at room temperature for 30 min. An additional 1.0 g of the Dess-Martin Periodinane was added, and the reaction mixture was stirred for an additional 30 min. A 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous bicarbonate (50 mL) was added slowly. The organic layer was collected, and the aqueous layer was extracted with dichloromethane (50 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduce pressure to give 5-phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde (1.87 g, 7.75 mmol, quantitative yield) as a pale yellow oil. The compound had an HPLC ret. time=2.09 min. (condition A).
Workup
- waitat room temperature for 30 min
- stirringthe reaction mixture was stirred for an additional 30 min
- additionwas added slowly
- customThe organic layer was collected
- extractionthe aqueous layer was extracted with dichloromethane (50 mL)
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-282bc2384a444b0c84a0f7abfc23669a
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09216972B2
Reaction notes
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