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

HRID 2085069Notes

Reaction equation

HRID 2085069 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 h. The catalyst was filtered, and the filtrate was concentrated to afford 1.89 g (45%) of the desired product. 1H NMR (CDCl3) δ 7.10-7.27 (m, 6H), 6.63-6.70 (m, 2H), 6.55 (s, 1H), 3.95-4.05 (m, 2H), 3.70 (s, 3H), 3.39 (m, 1H), 2.83-2.89 (m, 2H), 2.56-2.68 (m, 2H), 1.10 (m, 3H).

Workup

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

Sources & evidence

ORD record
ord-bbecc23a3fac4c00a5635bcea1327f30
Source dataset
uspto-grants-2004_04
Patent number
US06720315B2

Reaction notes

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