Vanillin → HCID 86605716, compound

HRID 2221574Notes

Reaction equation

HRID 2221574 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][OH:8])=[CH:5][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:3]=1.[O:15]=[CH:16][C:17]1[CH:25]=[CH:24][C:22](O)=[C:19]([O:20][CH3:21])[CH:18]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:21][O:20][C:19]1[CH:18]=[C:17]([CH:25]=[CH:24][C:22]=1[O:8][CH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:5]=1)[CH:16]=[O:15]

Participants

6

Reactant 4

HCID 1183VanillinHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23076503[3-Methyl-1-(pyridin-2-yl)-1H-pyrazol-4-yl]methanol

Product 1

HCID 86605716HCID 86605716, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (3-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)methanol (1.07 g), vanillin (0.85 g), tributylphosphine (1.70 g) and tetrahydrofuran (100 mL) as added 1,1′-(azodicarbonyl)dipiperidine (2.12 g) at room temperature, and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration. The filtrate was concentrated and the residue was subjected to silica gel column chromatography to give 3-methoxy-4-[(3-methyl-1-pyridin-2-yl-1H-pyrazol-4-yl)methoxy]benzaldehyde as colorless crystals (1.40 g, yield 77%) from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 141-142° C.

Workup

  1. customThe precipitated crystals were removed by filtration
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a73991e8d5e944e589ecac6bae551e04
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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