4-Isopropylaniline → 4-Isopropyl-N-(2,2-diethoxyethyl)aniline

HRID 610049

반응식

HRID 610049 반응식
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:11]([O:13][CH:14]([O:17][CH2:18][CH3:19])[CH2:15]Br)[CH3:12].C(=O)(O)[O-].[Na+]>C(O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][CH2:15][CH:14]([O:17][CH2:18][CH3:19])[O:13][CH2:11][CH3:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 74644-IsopropylanilineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium Bicarbonate

생성물 1

HCID 196009444-Isopropyl-N-(2,2-diethoxyethyl)aniline수율 90.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 4-isopropylaniline (7.6 mL, 56 mmol), 2-bromoacetaldehyde diethyl acetal (5.5 mL, 36 mmol) and sodium bicarbonate (4.8 g, 57 mmol) in ethanol (60 mL) was stirred at reflux for 3 days under argon. After cooling to room temperature, the ethanol was removed in vacuo and the product was partitioned between ether and water, washed sequentially with water and brine, and dried over sodium sulfate. After removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes) yielded 4-isopropyl-N-(2,2-diethoxyethyl) aniline (8.23 g, 90%).

후처리

  1. temperatureat reflux for 3 days under argon
  2. customthe ethanol was removed in vacuo
  3. customthe product was partitioned between ether and water
  4. washwashed sequentially with water and brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent in vacuo, flash chromatography (silica, 10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-4bc69996890742b593cb12a4b60e9adc
출처 데이터셋
uspto-grants-1999_12
특허 번호
US05998462

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