Acetic Acid → HCID 12710774, compound

HRID 595062Notes

Reaction equation

HRID 595062 reaction equation
C[O-].[Na+].C[O:5][C:6](=O)[CH2:7][S:8][CH:9]([CH3:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12].C(O)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:15][CH:9]1[CH:10]([C:11]([O:13][CH3:14])=[O:12])[C:6](=[O:5])[CH2:7][S:8]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 2777633HCID 2777633, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 12710774HCID 12710774, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of sodium methoxide (5.89 g, 109.2 mmol) in toluene (150 mL) was added methyl 3-(2-methoxy-2-oxoethylthio)butanoate (150 g, 72.8 mmol) dropwise. The resultant mixture was heated to reflux and stirred overnight. The resulting reaction mixture was cooled then poured into a mixture of 10.0 mL of acetic acid in 150.0 g of crushed ice. The solution was made basic (pH=8-9) by addition of saturated Na2CO3 and the resulting mixture extracted with ethyl acetate. The combined organic layers were then combined and washed with brine, dried over anhydrous Na2SO4, filtered, evaporated, and the residue purified by column chromatography (eluent: petroleum ether/ethyl acetate=20/1-5/1) to provide methyl 2-methyl-4-oxo-tetrahydrothiophene-3-carboxylate as a colorless oil (4.0 g, 32%).

Workup

  1. temperatureto reflux
  2. customThe resulting reaction mixture
  3. temperaturewas cooled
  4. extractionthe resulting mixture extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue purified by column chromatography (eluent: petroleum ether/ethyl acetate=20/1-5/1)

Sources & evidence

ORD record
ord-3fc09a8f3a8f434aa5f928cc82a8432e
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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