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

HRID 965852

반응식

HRID 965852 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 962Water용매

실험 절차

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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-a495954aa2bd448ba35baf9716c9dcc7
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951875B2

연결된 노트

불러오는 중…