Sodium Chloride → HCID 56617608, compound

HRID 2290428Notes

Reaction equation

HRID 2290428 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 mmols) of dry potassium thioacetate were added to a solution, cooled to 0° C., of 3.85 g (20.0 mmols) of tert.-butyl 4-chloroacetoacetate in 40 ml of anhydrous acetonitrile and the mixture was stirred at this temperature for 30 minutes. Thereafter, the mixture was poured into a mixture of NaCl solution and ethyl acetate, the organic phase was separated off and extracted with 2×30 ml of ethyl acetate and the extracts were washed with water and dried over MgSO4. After the solvent had been evaporated off in vacuo and the residue had been chromatographed 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 :0.2 (toluene:ethyl acetate 95:5).

Workup

  1. customthe organic phase was separated off
  2. extractionextracted with 2×30 ml of ethyl acetate
  3. washthe extracts were washed with water
  4. dry with materialdried over MgSO4
  5. customAfter the solvent had been evaporated off in vacuo
  6. customthe residue had been chromatographed on 60 g of silica gel (toluene:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-63384b8444ac46da84fb3a3e837bd1c8
Source dataset
uspto-grants-1986_10
Patent number
US04616084

Reaction notes

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