Acetic Acid → HCID 12710774, compound

HRID 625029Notes

Reaction equation

HRID 625029 reaction equation
CC[O-].[Na+].C[O:6][C:7](=O)[CH2:8][S:9][CH:10]([CH3:16])[CH2:11][C:12]([O:14][CH3:15])=[O:13].C(O)(=O)C>C(O)C.C(OCC)(=O)C>[CH3:16][CH:10]1[CH:11]([C:12]([O:14][CH3:15])=[O:13])[C:7](=[O:6])[CH2:8][S:9]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 2777633HCID 2777633, compound

Product 1

HCID 12710774HCID 12710774, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A three neck flask was charged with NaOEt (21%, 200 mL, 537 mmol) in ethanol. The solvent was removed under vacuum and to the residue was added toluene (500 mL). The mixture was heated to reflux and methyl 3-(2-methoxy-2-oxoethylthio)butanoate (92 g, 446 mmol) was added dropwise. After addition was complete, the mixture was refluxed for 4 hours. After cooling, the mixture was poured into a mixture of acetic acid (200 g) and crushed ice (200 g). The mixture was stirred overnight and then diluted with ethyl acetate (500 mL). The organic phase was separated and washed with saturated Na2CO3 and brine and then dried. The solvent was removed to afford crude methyl 2-methyl-4-oxo-tetrahydrothiophene-3-carboxylate (77.7 g, 99%). 1H NMR (CDCl3, 400 MHz) δ 11.23-11.15 (d, 1H), 7.27-7.16 (m, 2H), 4.33-4.12 (m, 2H), 3.95-3.68 (m, 2H). 3.60-3.15 (m, 1H), 2.60-2.20 (m, 1H).

Workup

  1. customThe solvent was removed under vacuum and to the residue
  2. additionwas added toluene (500 mL)
  3. temperatureThe mixture was heated
  4. temperatureto reflux
  5. additionAfter addition
  6. temperaturethe mixture was refluxed for 4 hours
  7. temperatureAfter cooling
  8. customThe organic phase was separated
  9. washwashed with saturated Na2CO3 and brine
  10. customdried
  11. customThe solvent was removed

Sources & evidence

ORD record
ord-0ae258a73a4748489e81a2cab93e9741
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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