Diethyl Ether → Ethyl 4,4-diethoxy-3-oxo-2-[(thiophen-2-yl)methylidene]butanoate

HRID 1759049Notes

Reaction equation

HRID 1759049 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[CH2:8]([O:10][CH:11]([O:20][CH2:21][CH3:22])[C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:9].C(OCC)C>N1CCCCC1.C1C=CC=CC=1>[C:2]1([CH:6]=[C:13]([C:12]([CH:11]([O:10][CH2:8][CH3:9])[O:20][CH2:21][CH3:22])=[O:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 73642-ThiophenecarboxaldehydeHCID 11138577Ethyl 4,4-diethoxy-3-oxobutanoate

Product 1

HCID 54013227Ethyl 4,4-diethoxy-3-oxo-2-[(thiophen-2-yl)methylidene]butanoate

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 241BenzeneSolvent

Procedure

A solution of thiophene-2-carbaldehyde (2.2430 g), ethyl 4,4-diethoxyacetoacetate (4.3648 g) and piperidine (4 drops) in benzene (20 ml) was refluxed under azeotropic dehydration for 4.5 hours. After cooling, to the resultant solution was added diethyl ether, and the solution was washed with water and dried. The solvent was removed from the reaction mixture to give oily ethyl 2-(2-thenylidene)-4,4-diethoxyacetoacetate.

Workup

  1. washthe solution was washed with water
  2. customdried
  3. customThe solvent was removed from the reaction mixture

Sources & evidence

ORD record
ord-54ee4ba96ae448c887503aff192dcaee
Source dataset
uspto-grants-1982_07
Patent number
US04338322

Reaction notes

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