Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate → Ethyl 4-(m-methoxyphenyl)-3-phenylbutyrate

HRID 2085056Notes

Reaction equation

HRID 2085056 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(O)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][CH:8]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 22602685Ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate

Product 1

HCID 22602704Ethyl 4-(m-methoxyphenyl)-3-phenylbutyrateYield 45.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 4-(m-methoxyphenyl)-3-phenyl-3-hydroxybutyrate (4.39 g, 13.98 mmol), palladium/carbon (10%, 2.5 g) hydrochloric acid (1.2 mL) in acetic acid (150 mL) was subjected to hydrogenation (50 psi) for 24 hours. The catalyst was filtered, and the filtrate was concentrated to afford the desired product (1.89 g; 45% yield). 1H NMR was consistent with the desired product.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a2051a1c379c4d038fdbe64ed1b9758c
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

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