Triethyl phosphonoacetate → HCID 69423040, compound

HRID 350274Notes

Reaction equation

HRID 350274 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:31]=[CH:30][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([CH:21]=O)[C:18]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[N:17]2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OP([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])(OCC)=O)C>CN(C)C=O>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH:20]=[C:19](/[CH:21]=[CH:40]/[C:41]([O:43][CH2:44][CH3:45])=[O:42])[C:18]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)=[N:17]2)=[CH:30][CH:31]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 23025043HCID 23025043, compound

Product 1

HCID 69423040HCID 69423040, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, oily, 1.10 g) was added to a solution of 1-(4-benzyloxybenzyl)-3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde (9.66 g) and ethyl diethylphosphonoacetate (5.46 ml) in N,N-dimethylformamide (150 ml) at 0° C., and the mixture was stirred at room temperature for 2 hours. Ice water was poured into the reaction mixture, and the resulting crystals were collected by filtration. After drying, recrystallization from ethyl acetate-hexane gave ethyl (E)-3-[1-(4-benzyloxybenzyl)-3-(4-fluorophenyl)-1H-pyrazol-4-yl]propenoate (10.60 g, yield: 93%). Melting point: 113–114° C.

Workup

  1. filtrationthe resulting crystals were collected by filtration
  2. customAfter drying
  3. customrecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-65373fa5e9474f64858791d6803ed35b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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