Reaction equation
P(Cl)(Cl)(Cl)=O.[O:6]1[C:10]2[CH2:11][N:12]([C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:13][CH2:14][C:9]=2[CH:8]=[CH:7]1.O.CN(C)[CH:31]=[O:32]>>[CH:31]([C:7]1[O:6][C:10]2[CH2:11][N:12]([C:15](=[O:27])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH2:13][CH2:14][C:9]=2[CH:8]=1)=[O:32]Participants
5
Procedure
To 30 ml of N,N-dimethylformamide, 0.33 ml (3.6 mmol) of phosphorus oxychloride was added under ice-cooling, followed by stirring at room temperature for 0.5 hours. To this mixture, a solution of 1.064 g (3.578 mmol) of 1-(5,7-dihydro-4H-furo[2,3-c]pyridin-6-yl)-6-phenylhexan-1-one in 20 ml of N,N-dimethylformamide was added, followed by overnight stirring at room temperature. After water was added, the reaction mixture was extracted with ethyl acetate 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel flush column chromatography (hexane/ethyl acetate=2/1 to 1/1) to yield the desired product.
Workup
- temperaturecooling
- waitfollowed by overnight
- stirringstirring at room temperature
- extractionthe reaction mixture was extracted with ethyl acetate 3 times
- dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe resulting crude product was purified by silica gel
- customflush column chromatography (hexane/ethyl acetate=2/1 to 1/1)
Sources & evidence
- ORD record
- ord-c9c77a809fa44d22bdb0076e300bbbae
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998433
Linked notes
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