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

HRID 1861524Notes

Reaction equation

HRID 1861524 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-352567031acc4b43afd607e158413fd2
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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