Methyl iodide → 2-(5-Ethyl-3-methyl-1,2-oxazol-4-yl)-1H-indole

HRID 434502Notes

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-4fac32ffd949448fbf237944b88db28c
Source dataset: uspto-grants-1983_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04397850

Reaction notes

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