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

HRID 965852

Reaction equation

HRID 965852 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-a495954aa2bd448ba35baf9716c9dcc7
Source dataset
uspto-grants-2005_10
Patent number
US06951875B2

Linked notes

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