Water → 5-Benzyloxy-4-t-butyl-2-formylbenzofuran
Reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][CH:20]=[CH:19][C:18]=2[C:22]=1[C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.CN(C)[CH:30]=[O:31]>>[CH2:6]([O:13][C:14]1[CH:15]=[CH:16][C:17]2[O:21][C:20]([CH:30]=[O:31])=[CH:19][C:18]=2[C:22]=1[C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Participants
Procedure
Under ice-cooling, 26.2 ml of phosphorus oxychloride was added dropwise to 17 ml of N,N-dimethylformamide, followed by a solution of 40.0 g of 5-benzyloxy-4-t-butylbenzofuran in 10 ml of N,N-dimethylformamide. After stirring at room temperature for 20 minutes, the mixture was heated at 80° C. for 2 hours. After cooling, the reaction solution was poured into water and extracted with ethyl acetate. The extracted layers were washed with a saturated aqueous sodium bicarbonate solution and then water, dried over anhydrous magnesium sulfate, and then concentrated. The concentrate was purified by silica gel column chromatography (in n-hexane containing 10%ethyl acetate) to give 16.2 g of 5-benzyloxy-4-t-butyl-2-formylbenzofuran as a pale yellow solid (yield 36%).
Workup
- temperatureUnder ice-cooling
- temperaturethe mixture was heated at 80° C. for 2 hours
- temperatureAfter cooling
- extractionextracted with ethyl acetate
- washThe extracted layers were washed with a saturated aqueous sodium bicarbonate solution
- dry with materialwater, dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe concentrate was purified by silica gel column chromatography (in n-hexane containing 10%ethyl acetate)
Sources & evidence
- ORD record
- ord-b936e20376b54177b320e5dc583d162e
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06403639B1
Reaction notes
Loading…