diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate → HCID 178476889, compound

HRID 2221534Notes

Reaction equation

HRID 2221534 reaction equation
C([O:8][C:9]1[C:13](/[CH:14]=[CH:15]/[P:16](=[O:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19])=[CH:12][N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]=1)C1C=CC=CC=1>[Pd].O1CCCC1>[OH:8][C:9]1[C:13]([CH2:14][CH2:15][P:16](=[O:23])([O:17][CH2:18][CH3:19])[O:20][CH2:21][CH3:22])=[CH:12][N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:10]=1

Participants

4

Reactant 1

HCID 86605708diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate

Product 1

HCID 178476889HCID 178476889, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Diethyl (E)-2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenylphosphonate (0.89 g), 5% palladium on carbon (1.0 g) and tetrahydrofuran (50 mL) were subjected to catalytic reduction under a hydrogen atmosphere and atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated to give diethyl 2-(3-hydroxy-1-phenyl-1H-pyrazol-4-yl)ethylphosphonate as colorless crystals (0.54 g, yield 76%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 121-122° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-95a6b32d7ffa427b823277ad30d43f12
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

Loading…