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

HRID 615450ノート

反応式

HRID 615450 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-60 °C

実験手順

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 1.6M 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.

後処理

  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

出典と根拠

ORDレコード
ord-8db071e0e25441d19fd3dd9c2ec8c58e
出典データセット
uspto-grants-1985_02
特許番号
US04499279

反応ノート

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