Methyl iodide → 2-(5-Ethyl-3-methyl-1,2-oxazol-4-yl)-1H-indole
Reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:16])[O:4][N:3]=1.[CH2:17]([Li])CCC.CCCCCC.CI>O1CCCC1>[CH2:16]([C:5]1[O:4][N:3]=[C:2]([CH3:1])[C:6]=1[C:7]1[NH:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:17]Participants
Conditions
- Temperature
- -60 °C
Procedure
A solution of 5 g (0.024 mole) of 2-(3,5-dimethyl-4-isoxazolyl)-indole in 100 ml of dry tetrahydrofuran is cooled to -60° and treated by dropwise addition with 32.4 ml of 1.6 M n-butyllithium in hexane (0.052 mole) maintaining temperature at -60° C. The resulting mixture is then stirred at -60° C. for 30 min. and then treated by dropwise addition of 4.01 g (0.028 mole) of methyl iodide in 10 ml dry tetrahydrofuran. The resulting mixture is stirred at -60° for 4 hours and quenched by the addition of 6 ml saturated ammonium chloride solution. The mixture is then warmed to room temperature and treated with 50 ml of water and extracted with methylene chloride. The organic layers are dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting oil is then purified by filtration through silica gel to give 2-(5-ethyl-3-methyl-4-isoxazolyl)-indole as a viscous oil.
Workup
- stirringThe resulting mixture is stirred at -60° for 4 hours
- customquenched by the addition of 6 ml saturated ammonium chloride solution
- temperatureThe mixture is then warmed to room temperature
- additiontreated with 50 ml of water
- extractionextracted with methylene chloride
- dry with materialThe organic layers are dried over magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- filtrationThe resulting oil is then purified by filtration through silica gel
Sources & evidence
- ORD record
- ord-fb0bcb74adb142be8193908c0de4f02a
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04336379
Reaction notes
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