Water → HCID 53860328, compound

HRID 1901765Notes

Reaction equation

HRID 1901765 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=O.[CH3:13][C:14]([CH:16]([O:19][CH3:20])[O:17][CH3:18])=[O:15].[OH-].[K+].O>C(O)C>[CH3:18][O:17][CH:16]([O:19][CH3:20])[C:14](=[O:15])[CH:13]=[CH:1][C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 80650Pyruvic aldehyde dimethyl acetalHCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

Product 1

HCID 53860328HCID 53860328, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-formyl-2,2'-bithiophene (4.0 g) in ethanol (120 ml) was added dimethoxymethyl methyl ketone (3 ml). Potassium hydroxide aqueous solution (50%) was added dropwisely into the solution mixture at 16° C. Color changed from yellowish brown into dark green, then dark brown. Yellow solid was formed during the reaction. Water was added. Solid residue was filtered and washed with water, redissolved in acetone and separated by silica gel chromatography eluted with ethyl acetate/n-hexane (1:9). Yellowish crystals 1.88 g were obtained, melting point 74° C.

Workup

  1. customYellow solid was formed during the reaction
  2. filtrationSolid residue was filtered
  3. washwashed with water
  4. dissolutionredissolved in acetone
  5. customseparated by silica gel chromatography
  6. washeluted with ethyl acetate/n-hexane (1:9)

Sources & evidence

ORD record
ord-7259a2d5780c42eb8a8c6b791aeaeb18
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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