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

HRID 904616노트

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HRID 904616 반응식
[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]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 202701232-(3,5-Dimethyl-1,2-oxazol-4-yl)-1H-indoleHCID 178418339Butyllithium

생성물 1

HCID 133756472-(5-Ethyl-3-methyl-1,2-oxazol-4-yl)-1H-indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-60 °C

실험 절차

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.

후처리

  1. stirringThe resulting mixture is stirred at -60° for 4 hours
  2. customquenched by the addition of 6 ml saturated ammonium chloride solution
  3. temperatureThe mixture is then warmed to room temperature
  4. additiontreated with 50 ml of water
  5. extractionextracted with methylene chloride
  6. dry with materialThe organic layers are dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. filtrationThe resulting oil is then purified by filtration through silica gel

출처 및 근거

ORD 기록
ord-9cc632669fdc4d15957503a1dfb011cf
출처 데이터셋
uspto-grants-1983_12
특허 번호
US04419353

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