Ethyl Thioglycolate → HCID 20364852, compound

HRID 1678919Notes

Reaction equation

HRID 1678919 reaction equation
[CH2:1]([O:3][CH:4]([O:12][CH2:13][CH3:14])/[CH:5]=[CH:6]/[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[Na].[C:16](OCC)(=[O:19])[CH2:17][SH:18]>C(O)C>[CH2:13]([O:12][CH:4]([O:3][CH2:1][CH3:2])[CH:5]1[CH:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:16](=[O:19])[CH2:17][S:18]1)[CH3:14]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 5360545SodiumHCID 5826656HCID 5826656, compound

Product 1

HCID 20364852HCID 20364852, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material is prepared as follows: 8.65 g of ethyl 4,4-diethoxycrotonate are added at once at 0° to the mixture prepared from 1 g of pulverized sodium, 40 ml of ethanol and 4.94 ml of ethyl thioglycolate, evaporating the mixture after stirring it at room temperature and adding 43 ml of dimethylsulfoxide and 20 ml of dimethylformamide. The mixture is stirred at 0° for one-half hour and at room temperature for 2 hours, poored into cold water and extracted with diethyl ether. The aqueous layer is acidified with 21.7 ml of cold 2N hydrochloric acid and extracted with diethyl ether. The extract is dried and evaporated, to yield the ethyl 2-diethoxymethyl-4-oxo-tetrahydrothiophene-3-carboxylate showing in the IR spectrum-bands at 1750, 1725, 1660, 1615 cm-1.

Workup

  1. customThe starting material is prepared
  2. customevaporating the mixture
  3. additionadding 43 ml of dimethylsulfoxide and 20 ml of dimethylformamide
  4. stirringThe mixture is stirred at 0° for one-half hour and at room temperature for 2 hours
  5. extractionextracted with diethyl ether
  6. extractionextracted with diethyl ether
  7. customThe extract is dried
  8. customevaporated

Sources & evidence

ORD record
ord-464c59960d434d49ab36ec5d57d1aac7
Source dataset
uspto-grants-1978_03
Patent number
US04077980

Reaction notes

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