Sodium Chloride → HCID 56617608, compound

HRID 1905094Notes

Reaction equation

HRID 1905094 reaction equation
C([O-])(=[S:3])C.[K+].Cl[CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=O.[Na+].[Cl-].[C:20]([O:23]CC)(=O)[CH3:21]>C(#N)C>[C:20]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[S:3])(=[O:23])[CH3:21]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 2724514tert-Butyl 4-chloro-3-oxobutyrateHCID 23670855Potassium ethanethioate

Product 1

HCID 56617608HCID 56617608, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.40 g (21.0 mmol) of dry potassium thioacetate were added to a solution, which had been cooled to 0° C., of 3.85 g (20.0 mmol) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile, and the mixture was stirred at this temperature for 30 min. It was then poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off, extraction with 2×30 ml of ethyl acetate was carried out, and the extract was washed with water and dried over MgSO4. After evaporation of the solvent in vacuo and chromatography of the residue on 60 g of silica gel (toluene:ethyl acetate 95:5), 3.87 g (83%) of the title compound were obtained as a colorless oil, Rf: 0.24 (toluene:ethyl acetate 95:5).

Workup

  1. customthe organic phase was separated off
  2. extractionextraction with 2×30 ml of ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over MgSO4
  5. customAfter evaporation of the solvent in vacuo and chromatography of the residue on 60 g of silica gel (toluene:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-8063340909ba4a3fa35af49d5670c993
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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