4-[4-(2-Hydroxyethyl)phenyl]-4-oxo-butyric acid methyl ester → 4-[4-(2-Hydroxyethyl)phenyl]butyric acid methyl ester

HRID 1516038Notes

Reaction equation

HRID 1516038 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10][CH:9]=1)=O>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][OH:16])=[CH:12][CH:13]=1

Participants

4

Reactant 1

HCID 596786384-[4-(2-Hydroxyethyl)phenyl]-4-oxo-butyric acid methyl ester

Product 1

HCID 596786304-[4-(2-Hydroxyethyl)phenyl]butyric acid methyl esterYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of Example 1A (2.50 g, 11 mmol), 10% Pd/C (0.25 g, 0.23 mmol of Pd metal) in anhydrous methanol (25 mL) was first degassed to remove air (two vacuum/H2 cycles) after which it was capped and a balloon filled with 112 was applied to it for 12 hours. After this time the reaction mixture was filtered through diatomaceous earth (Celite®) and the filtrate was concentrated under reduced pressure to give 2.32 g of crude material. Column chromatography [silica gel; eluent hexanes-ethyl acetate (2:1)] provided the desired product (0.92 g, 39%). 1H (CDCl3) δ(ppm): 1.91-1.96 (m, 2H); 2.32 (t, 2H); 2.62 (t, 2H); 2.83 (t, 2H); 3.66 (s, 3H); 3.85 (t, 2H); 7.11-7.15 (m, 4H).

Workup

  1. customto remove air (two vacuum/H2 cycles) after which it
  2. customwas capped
  3. additiona balloon filled with 112
  4. filtrationAfter this time the reaction mixture was filtered through diatomaceous earth (Celite®)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customto give 2.32 g of crude material

Sources & evidence

ORD record
ord-e5fb3e5cbc844de28dc748ade4d520ce
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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