Acetone → 2-Methyl-7-benzyloxy indole

HRID 480578ノート

反応式

HRID 480578 の反応式
[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

参加物

7

反応物 4

HCID 180AcetoneHCID 7498Benzyl Bromide2 回HCID 10796Cesium carbonate2 回HCID 187652222-methyl-1H-indol-7-ol

生成物 1

HCID 187653452-Methyl-7-benzyloxy indole収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c54f0a7061fa4f24b3aeccd3efeb7125
出典データセット
uspto-grants-2003_11
特許番号
US06653304B2

反応ノート

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