Water → Methyl 2-methyl-2-(4-methylsulfonylphenacyl)acetoacetate

HRID 1415764Notes

Reaction equation

HRID 1415764 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([C:9](=[O:19])[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[H-].[Na+].[CH3:24]I.O>O1CCCC1>[CH3:24][C:11]([CH2:10][C:9]([C:8]1[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:21][CH:20]=1)=[O:19])([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

Product 1

HCID 21862826Methyl 2-methyl-2-(4-methylsulfonylphenacyl)acetoacetateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.65 g (2.1 mmol) of methyl 2-(4-methylsulfonylphenacyl)acetoacetate [prepared as described in Example 43(ii)] was dissolved in 20 ml of anhydrous tetrahydrofuran, and 92 mg (2.3 mmol) of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting solution, whilst ice-cooling and under a nitrogen atmosphere. The mixture was stirred for 10 minutes, after which 1.1 ml (2.5 mmol) of methyl iodide were added, whilst ice-cooling, and the mixture was stirred for 2 hours. At the end of this time, water was added to the mixture, which was then extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 2:3 by volume mixture of ethyl acetate and hexane, to give 0.54 g (yield 80%) of the title compound as a slightly yellow powder.

Workup

  1. temperaturecooling and under a nitrogen atmosphere
  2. temperaturecooling
  3. stirringthe mixture was stirred for 2 hours
  4. extractionwas then extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with a saturated aqueous solution of sodium chloride
  7. dry with materialafter which it was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed by distillation under reduced pressure
  9. washeluted with a 2:3 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-23a6da484a3041169afc61e08fe9ba23
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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