Acetone → 2-Methyl-7-benzyloxy indole

HRID 480578노트

반응식

HRID 480578 반응식
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[OH:11].CC(C)=O.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CCOC(C)=O.O>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[O:11][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 7498Benzyl Bromide2회HCID 10796Cesium carbonate2회HCID 187652222-methyl-1H-indol-7-ol

생성물 1

HCID 187653452-Methyl-7-benzyloxy indole수율 81%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

To the compound from step A, acetone (15 mL) was added followed by benzyl bromide (670 μL, 5.6 mmol) and Cs2CO3 (1.8 g, 5.6 mmol) and the reaction mixture stirred at RT for 18 h. A second aliquot of BnBr (140 μL) and Cs2CO3 (380 mg) was added and stirring continued for 24 h. The reaction mixture was poured into EtOAc and water, the layers were separated, and the aqueous layer was further extracted with EtOAc (3×50 mL). The combined organic extracts were washed with 1N NaOH and water and dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (hexanes then 5% EtOAc/hex) afforded 2-methyl-7-benzyloxy indole as an unstable solid (898 mg, 81% yield). 1H NMR impure; 238.17, M+H.

후처리

  1. stirringstirring
  2. waitcontinued for 24 h
  3. customthe layers were separated
  4. extractionthe aqueous layer was further extracted with EtOAc (3×50 mL)
  5. washThe combined organic extracts were washed with 1N NaOH and water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography (hexanes

출처 및 근거

ORD 기록
ord-c54f0a7061fa4f24b3aeccd3efeb7125
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06653304B2

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