Diethyl Malonate → HCID 20155910, compound

HRID 363980Notes

Reaction equation

HRID 363980 reaction equation
C(OCC)(=O)[CH2:2][C:3](OCC)=[O:4].[Na].[S:13]1[CH:17]=[CH:16][N:15]=[C:14]1[CH:18]=[CH:19][C:20](=[O:22])[CH3:21].[OH-].[K+]>C(O)C>[OH:4][C:3]1[CH2:2][CH:18]([C:14]2[S:13][CH:17]=[CH:16][N:15]=2)[CH2:19][C:20](=[O:22])[CH:21]=1

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 54371892HCID 54371892, compound

Product 1

HCID 20155910HCID 20155910, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

Diethyl malonate (1.16 g) was added to a solution of sodium (158 mg) in dry absolute ethanol (10 ml) and the mixture was heated to reflux. 1-(2-Thiazolyl)but-1-en-3-one (1.0 g) in dry absolute ethanol (5 ml) was added dropwise to the solution. After refluxing for 2.5 hr, an aqueous potassium hydroxide solution (862 mg in 12 ml) was added and the mixture was extracted with diethyl ether. The aqueous layer was heated to 70° C. and neutralised with dilute hydrochloric acid and the water was then evaporated under reduced pressure. The residue was extracted with dry dimethylformamide. Evaporation of the solvent gave 3-hydroxy-5-(2-thiazolyl)cyclohex-2-en-1-one.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter refluxing for 2.5 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. customthe water was then evaporated under reduced pressure
  5. extractionThe residue was extracted with dry dimethylformamide
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6c71853065884cd78f2e56fc3d80a0a7
Source dataset
uspto-grants-1986_08
Patent number
US04604132

Reaction notes

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