Methyl pyruvate → Dimethyl 3-hydroxy-4-methyl-2,5-thiophene dicarboxylate

HRID 1493357Notes

Reaction equation

HRID 1493357 reaction equation
C[O-].[Na+].[Na].[C:5](OC)(=[O:9])[C:6]([CH3:8])=O.[S:12]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH2:13][C:14]([O:16][CH3:17])=[O:15]>CO>[OH:9][C:5]1[C:6]([CH3:8])=[C:13]([C:14]([O:16][CH3:17])=[O:15])[S:12][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 11748Methyl pyruvateHCID 852331,1'-Dimethyl 2,2'-thiobis(acetate)HCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 54691274Dimethyl 3-hydroxy-4-methyl-2,5-thiophene dicarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of sodium methoxide from sodium (5.4 g) in methanol (100 ml) was added a solution of methyl pyruvate (24 g) and dimethyl thiodiacetate (41.83 g) in methanol (50 ml). The reaction was stirred at room temperature for 2 days, and then added to ice water (500 ml). After neutralization with 5N HCl and extraction with chloroform, the organics were washed with brine, dried over anhydrous magnesium sulphate, filtered and the solvent evaporated to give a solid, m.p 95°-97° ex methanol.

Workup

  1. extractionAfter neutralization with 5N HCl and extraction with chloroform
  2. washthe organics were washed with brine
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customto give a solid, m.p 95°-97° ex methanol

Sources & evidence

ORD record
ord-4c20283324414675a214e76fea5ed202
Source dataset
uspto-grants-1991_06
Patent number
US05021449

Reaction notes

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