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

HRID 1861531Notes

Reaction equation

HRID 1861531 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]>[Ni].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 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of ethyl-2,3-epoxy-3-(4benzyloxyphenyl)propionate of the formula (9) (125 g) obtained according to the procedure described in step (ii) above, Raney Nickel (12.5 g) and 1,4-dioxane (750 ml) was hydrogenated at room temperature at 30-40 psi of hydrogen pressure for a period of 8-10 hours. 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-f83bdae37bf848d6b438d84500a56973
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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