Dimethylformamide → HCID 86602519, compound

HRID 30677Notes

Reaction equation

HRID 30677 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5]([CH:13]=O)[CH:4]=[N:3]1.[H-].[Na+].C(OP([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])(OCC)=O)C.CN(C)C=O>O>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[C:5](/[CH:13]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 838176701-methyl-5-(3-pyridinyl)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 86602519HCID 86602519, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-methyl-5-(3-pyridinyl)-1H-pyrazole-4-carbaldehyde (750 mg), sodium hydride (60% in oil, 176 mg), ethyl diethylphosphonoacetate (1.08 g) and N,N-dimethylformamide (8 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave ethyl (2E)-3-[1-methyl-5-(3-pyridinyl)-1H-pyrazol-4-yl]acrylate (770 mg, 75%) as pale-yellow prism crystals. melting point: 159-160° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5f56c9601e4c46b8ba8c5ea72057fca1
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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