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

HRID 1354886Notes

Reaction equation

HRID 1354886 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-(4-benzyloxyphenyl)propionate of the formula (9) (125 g) obtained according to the procedure described in step (ii) above. Railey 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-83605cd5b505483fb1653a23cdfd7726
Source dataset
uspto-grants-2007_05
Patent number
US07223881B2

Reaction notes

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