Methyl iodide → 4-(Benzyloxy)-1-methyl-1H-indole

HRID 1623553노트

반응식

HRID 1623553 반응식
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:21]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 884654-(phenylmethoxy)-1H-indole

생성물 1

HCID 247769014-(Benzyloxy)-1-methyl-1H-indole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 4-benzyloxy-1H-indole (CAS#20289-26-3, 10.85 g, 48.6 mmol) in N,N-dimethylformamide (200 mL) at 0° C., was added sodium hydride (60% dispersion in oil, 2.24 g, 55.9 mmol). The reaction was permitted to stir for 15 minutes at 0° C. Then iodomethane (3.19 mL, 51.0 mmol) was added to the reaction mixture. The reaction was put at room temperature and permitted to stir 30 minutes. The reaction was then quenched with saturated aqueous ammonium chloride. The mixture was diluted with water and extracted with diethyl ether. The layers were separated and the aqueous layer was then extracted two additional times with diethyl ether. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 4-benzyloxy-1-methyl-1H-indole; MS: (ES+) m/z 238.4 (M+H)+.

후처리

  1. customwas put at room temperature
  2. stirringto stir 30 minutes
  3. customThe reaction was then quenched with saturated aqueous ammonium chloride
  4. additionThe mixture was diluted with water
  5. extractionextracted with diethyl ether
  6. customThe layers were separated
  7. extractionthe aqueous layer was then extracted two additional times with diethyl ether
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6bc757ee3ca348538abb1ddd831c2cac
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778972B2

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