Methanol → Ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate

HRID 1360544Notes

Reaction equation

HRID 1360544 reaction equation
[Na].[C:2]([O:8][CH3:9])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].[CH:10]([S:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[CH2:11].[CH3:21]O>>[C:15]1([S:12]([CH2:10][CH2:11][CH:3]([C:4](=[O:5])[CH3:6])[C:2]([O:8][CH2:9][CH3:21])=[O:7])(=[O:13])=[O:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 7757Methyl acetoacetateHCID 79664Phenyl vinyl sulfoneHCID 5360545Sodium

Product 1

HCID 66959018Ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate

Procedure

Sodium metal (23 mg, 1 mmol) was added to 25 mL of methanol. After the sodium metal was consumed, methyl acetoacetate (1.16 g, 10 mmol) was added to the mixture and stirred for 15 minutes. A solution of phenyl vinyl sulfone (1.68 g, 10 mmol) was added dropwise to the solution and maintained for several hours. The slightly yellow solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and washed with saturated aqueous ammonium chloride. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to afford a clear oil. The material was purified via flash column chromatography on silica gel (eluting with hexane:ethyl acetate in a gradient from 3:2 to 2:3) to afford 1.40 g of ethyl 2-(2-benzenesulfonylethyl)-3-oxo-butyrate.

Workup

  1. customAfter the sodium metal was consumed
  2. temperaturemaintained for several hours
  3. concentrationThe slightly yellow solution was concentrated under reduced pressure
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with saturated aqueous ammonium chloride
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a clear oil
  12. customThe material was purified via flash column chromatography on silica gel (
  13. washeluting with hexane

Sources & evidence

ORD record
ord-bbaaeaf1a25849f6a63d885acc778c90
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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