Ethyl-2,3-epoxy-3-(4-benzyloxyphenyl)propionate → 3-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl ester

HRID 1861521Notes

Reaction equation

HRID 1861521 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]1[O:21][CH:6]1[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH3:2].[H][H]>[Pd].O1CCOCC1>[OH:21][CH:5]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:22]

Participants

5

Reactant 2

HCID 11277925Ethyl-2,3-epoxy-3-(4-benzyloxyphenyl)propionate2×HCID 178418361HCID 178418361, compound

Product 1

HCID 151861533-(4-Benzyloxyphenyl)-2-hydroxypropionic acid ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl-2,3-epoxy-3-(4-benzyloxyphenyl)propionate of the formula (9) (125 g) obtained according to the procedure described in step (ii) above, 5% Pd/C catalyst (12.5 g) and 1,4-dioxane (750 ml) was hydrogenated at room temperature at 5-10 psi of hydrogen pressure for a period of 10-15 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the catalyst was filtered and the solvent was removed under reduced pressure to afford the title compound of the formula (10) (100-105 g, 80-83%).

Workup

  1. customobtained
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-549de8f20f4441b383b0aa28b36f65cf
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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