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

HRID 610049

反応式

HRID 610049 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4bc69996890742b593cb12a4b60e9adc
出典データセット
uspto-grants-1999_12
特許番号
US05998462

関連ノート

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