Benzyl Bromide → 1h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-

HRID 2256265노트

반응식

HRID 2256265 반응식
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=2)[CH3:2].[H-].[Na+].CCCCCC.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[C:24]1([CH2:23][N:4]2[C:5]3[C:10](=[C:9]([N+:12]([O-:14])=[O:13])[CH:8]=[CH:7][CH:6]=3)[CH:11]=[C:3]2[CH2:1][CH3:2])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

참가 물질

7

반응물 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 24758Sodium hydrideHCID 130479942-ethyl-4-nitro-1H-indole

생성물 1

HCID 105407101h-Indole,2-ethyl-4-nitro-1-(phenylmethyl)-수율 91%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

2-Ethyl-4-nitro-1H-indole (4.75 g, 25 mmol) was added to a mixture of 1.0 g (25 mmol) of 60% NaH/mineral oil (washed with hexane before adding DMF) in 40 ml DMF. After 45 minutes, 3.0 ml (25 mmol) of benzyl bromide was added. The mixture was stirred at room Temperature for four hours, diluted with water, and extracted with EtOAc. The EtOAc solution was washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane to give 6.36 g (91%) of 1-Phenylmethyl-2-ethyl-4-nitro-1H-indole as an oil.

후처리

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/Hexane

출처 및 근거

ORD 기록
ord-402a19add0684fdebc9d73f2940ee8e0
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05654326

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