Pyridine → trans-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-(4-fluoro-3-isopropenylbenzyl)amine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:11][CH:12]=[CH:13][C:14]#[C:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:10])=[CH:4][C:3]=1[CH2:20][CH:21](O)C.P(Cl)(Cl)(Cl)=O.N1C=CC=C[CH:30]=1>>[CH3:19][C:16]([CH3:17])([CH3:18])[C:15]#[C:14]/[CH:13]=[CH:12]/[CH2:11][N:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:20]([CH3:21])=[CH2:30])[CH:4]=1)[CH3:10]Participants
4
Conditions
- Temperature
- 110 °C
Procedure
Compound 29 (0.55 g; 1.73 mmol) and phosphorus oxychloride (1.33 g; 8.65 mmol) were dissolved in pyridine (25 ml). The solution was stirred for 3 hours at 110° C., and left to cool to room temperature. The mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with diethyl ether (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 0.17 g of the target compound (yield: 32.8%).
Workup
- waitleft
- temperatureto cool to room temperature
- additionThe mixture was poured into ice+saturated aqueous sodium bicarbonate solution
- extractionfollowed by extraction with diethyl ether (100 ml)
- washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
- dry with materialwith saturated brine, and dried over sodium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1)
Sources & evidence
- ORD record
- ord-f52098f454ae453fb35cb42373c1c55e
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586633B1
Reaction notes
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