HCID 59105415, compound → HCID 67753502, compound

HRID 653626Notes

Reaction equation

HRID 653626 reaction equation
C([O:8][C:9]1[C:10]([CH3:23])=[N:11][N:12]([CH3:22])[C:13]=1/[C:14](=[CH:19]\[O:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])C1C=CC=CC=1>CO.[Pd]>[CH3:22][N:12]1[C:13](/[C:14](=[CH:19]\[O:20][CH3:21])/[C:15]([O:17][CH3:18])=[O:16])=[C:9]([OH:8])[C:10]([CH3:23])=[N:11]1

Participants

4

Reactant 1

HCID 59105415HCID 59105415, compound

Product 1

HCID 67753502HCID 67753502, compoundYield 949%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-methyl 2-(4-benzyloxy-1,3-dimethylpyrazol-5-yl)-3-methoxyacrylate (56 g, 17.7 mmol) in methanol (560 ml) was subjected to hydrogenation in the presence of 5% powdered palladium/carbon (5.3 g). When the reaction completed, the mixture was filtered and the filtrate was concentrated under reduced pressure. The residue, when recrystallized from a solvent system of methanol/ethyl acetate/n-hexane, gave a purified (E)-methyl 2-(1,3-dimethyl-4-hydroxypyrazol-5-yl)-3-methoxyacrylate (38 g, yield 94.8 %). M.p.=172.7°-173.4 ° C.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue, when recrystallized from a solvent system of methanol/ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-173354774818440c99fb229bf7beaa03
Source dataset
uspto-grants-1992_07
Patent number
US05128350

Reaction notes

Loading…