Dimethylformamide → ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate

HRID 1295248Notes

Reaction equation

HRID 1295248 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]=O)[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:26][CH2:27][CH2:28]P(OCC)(OCC)=O)(=[O:25])[CH3:24].CN(C)C=O.[H-]>O>[CH2:1]([N:8]1[CH:12]=[C:11](/[CH:13]=[CH:24]/[C:23]([O:26][CH2:27][CH3:28])=[O:25])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 166653HydrideHCID 124696282-(Diethoxyphosphoryl)ethyl acetateHCID 229307681-benzyl-3-(benzyloxy)-1H-pyrazole-4-carbaldehyde

Product 1

HCID 69421683ethyl(E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoateYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-benzyl-3-benzyloxy-1H-pyrazole-4-carbaldehyde (12.90 g), diethylphosphonoethyl acetate (9.60 ml) and N,N-dimethylformamide (200 ml) was added hydride (60% in oil, 1.94 g) at 0° C., and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was poured into water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dilute hydrochloric acid, washed successively with saturated brine, dried (MgSO4) and concentrated. The obtained crystals were collected by filtration to give ethyl (E)-3-(1-benzyl-3-benzyloxy-1H-pyrazol-4-yl)propenoate (14.50 g, yield 91%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 88–89° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed successively with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-8bc7b9e224904d77bc089c0d72c48e33
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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