Sodium Thiosulfate → Methyl 2-(4-methylthiophenacyl)acetoacetate

HRID 856830Notes

Reaction equation

HRID 856830 reaction equation
CS(C1C=CC([C:9](=O)[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=CC=1)(=O)=O.Cl[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29](OO)=O)[CH:24]=1.[S:33]([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH3:29][C:25]1[CH:24]=[CH:23][C:28]([C:9](=[S:33])[CH2:10][CH:11]([C:16]([CH3:18])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

Product 1

HCID 54143420Methyl 2-(4-methylthiophenacyl)acetoacetateYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

43(ii) Methyl 2-(4-methylsulfonylphenacyl)acetoacetate 4.42 g (15.8 mmol) of methyl 2-(4-methylthiophenacyl) acetoacetate [prepared as described in step (i) above] were dissolved in 150 ml of methylene chloride, and 7.77 g (31.5 mmol) of 70% m-chloroperbenzoic acid were added to the resulting solution, whilst ice-cooling. The mixture was then stirred at room temperature for 1 hour. 30 ml of a 10% w/v aqueous solution of sodium thiosulfate were added to the mixture, and the mixture was vigorously shaken, after which it separated into liquid phases. The organic layer was separated and washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate and the solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:1 by volume mixture of ethyl acetate and hexane, to give 3.65 g (yield 74%) of the title compound as a slightly yellow powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was vigorously shaken
  3. customafter which it separated into liquid phases
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  6. dry with materialafter which it was dried over anhydrous magnesium sulfate
  7. customthe solvent was then removed by distillation under reduced pressure
  8. washeluted with a 1:1 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-25ebe37eefae4f029e39fdd1e1c3b667
Source dataset
uspto-grants-2006_12
Patent number
USRE039420E1

Reaction notes

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