2,5-Dimethoxybenzaldehyde → HCID 68470985, compound

HRID 1808272Notes

Reaction equation

HRID 1808272 reaction equation
Cl.[C:2]1([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:18]=1[CH:19]=O.CC([O-])(C)C.[K+]>CN(C=O)C>[C:2]1([C:8]2[CH:13]=[C:12]([CH:14]=[CH:19][C:18]3[CH:21]=[C:22]([O:25][CH3:26])[CH:23]=[CH:24][C:17]=3[O:16][CH3:15])[CH:11]=[CH:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 667262,5-DimethoxybenzaldehydeHCID 23665647Potassium tert-butoxideHCID 67438976HCID 67438976, compound

Product 1

HCID 68470985HCID 68470985, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 2-phenyl-4-methylpyridine hydrochloride (1 g, 4.9 mmol) and 2,5-dimethoxybenzaldehyde (1.2 g, 7.3 mmol) in anhydrous DMF (40 ml), solid t-BuOK (2 g, 18 mmol) was added. The resulting mixture was stirred overnight at 80° C. under nitrogen. After evaporating DMF, Et2O was added thereto and the precipitate was filtered and washed with water. The solid was purified by column chromatography (SiO2, CH2Cl2/MeOH, 99/1) to afford 0.6 g (39%) of the desired compound as a yellow solid.

Workup

  1. additionwas added
  2. customAfter evaporating DMF, Et2O
  3. additionwas added
  4. filtrationthe precipitate was filtered
  5. washwashed with water
  6. customThe solid was purified by column chromatography (SiO2, CH2Cl2/MeOH, 99/1)

Sources & evidence

ORD record
ord-24fd6422eb974bed958c345e085ffde0
Source dataset
uspto-grants-2013_01
Patent number
US08357800B2

Reaction notes

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