4-Methylbenzaldehyde → 2-(2-p-Tolyl-vinyl)-pyridine 1-oxide

HRID 965852

反応式

HRID 965852 の反応式
[N+:1]1([O-:8])[C:2]([CH3:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.C([O-])(C)(C)C.[K+].[C:15]1([CH3:23])[CH:20]=[CH:19][C:18]([CH:21]=O)=[CH:17][CH:16]=1>C(O)CCC.O>[C:15]1([CH3:23])[CH:20]=[CH:19][C:18]([CH:21]=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N+:1]=2[O-:8])=[CH:17][CH:16]=1

参加物

6

反応物 3

HCID 77254-MethylbenzaldehydeHCID 136022-Methylpyridine 1-oxideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 695921292-(2-p-Tolyl-vinyl)-pyridine 1-oxide収率 55%

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 962Water溶媒

実験手順

To a refluxing solution of 2-picoline-1-oxide (10.9 g, 100 mmol), potassium tert.-butanolate ( 11.2 g, 100 mmol) in butanol (100 ml) was added portion-wise p-tolualdehyde (12.0 g, 100 mmol). Reflux was maintained for 90 min. Then the mixture was cooled to rt, diluted with H2O (100 ml) and extracted with CH2Cl2. The combined organic phases were dried with MgSO4, concentrated and chromatographed (SiO2 with CH2Cl2/MeOH=95:5) to provide the title compound (11.6 g, 55%) as a yellow solid material. MS: m/e=211 (M+).

後処理

  1. temperatureReflux
  2. temperaturewas maintained for 90 min
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. concentrationconcentrated
  6. customchromatographed (SiO2 with CH2Cl2/MeOH=95:5)

出典と根拠

ORDレコード
ord-a495954aa2bd448ba35baf9716c9dcc7
出典データセット
uspto-grants-2005_10
特許番号
US06951875B2

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