Methanol → (4-Methylsulfonyl-phenyl)-oxo-acetic acid ethyl ester

HRID 600974Notes

Reaction equation

HRID 600974 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10](SC)=[CH:9][CH:8]=1)=[O:6])[CH3:2].O[O:17][S:18]([O-:20])=O.[K+].[CH3:22]O>O>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:18]([CH3:22])(=[O:20])=[O:17])=[CH:9][CH:8]=1)=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 2758911Ethyl 4-thiomethylbenzoylformateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 13623455(4-Methylsulfonyl-phenyl)-oxo-acetic acid ethyl esterYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(4-Methylsulfanyl-phenyl)-oxo-acetic acid ethyl ester (1.09 g, 4.86 mmol) and oxone (8.96 g, 14.6 mmol) were combined in a mixture of water (2.2 mL) and methanol (22 mL) and stirred for 16 h. The volatiles were evaporated in vacuo and the residue was treated with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% ethyl acetate/hexanes) to afford (4-methanesulfonyl-phenyl)-oxo-acetic acid ethyl ester as a white solid (261 mg, 21%): H1-NMR (400 MHz, CDCl3) δ=1.46 (3H, t, J=7.1 Hz), 3.10 (3H, s), 4.48 (2H, q, J=7.1 Hz), 8.09 (2H, m), 8.23 (2H, m).

Workup

  1. customThe volatiles were evaporated in vacuo
  2. additionthe residue was treated with water (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (Merck silica gel 60, 40-63 μm; 33% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-25d3a397f76a447a9d8512c162a17396
Source dataset
uspto-grants-2011_03
Patent number
US07902248B2

Reaction notes

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