2-Thiophenecarboxaldehyde → HCID 785281, compound

HRID 1382858Notes

Reaction equation

HRID 1382858 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.[C:8]([CH2:16][CH2:17][C:18]([OH:20])=[O:19])(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OC(=O)C)(=O)C>C(Cl)(Cl)Cl>[C:9]1([C:8]2[O:20][C:18](=[O:19])[C:17](=[CH:6][C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 7918Acetic AnhydrideHCID 728713-Benzoylpropionic acid

Product 1

HCID 785281HCID 785281, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

Thiophene-2-carboxaldehyde (27.4 cc), 3-benzoylpropionic acid (44.5 g), acetic anhydride (71 cc) and fused potassium acetate (20.5 g) are heated overnight at 80° C. The mixture is cooled to 40° C., chloroform is added and then poured onto crushed ice. Extraction is carried out with chloroform, the organic phase is washed with a decinormal sodium hydroxide solution, it is dried over magnesium sulfate and evaporated under reduced pressure. The residue is stirred for 45 minutes in 40°-60° petroleum spirit, filtered and dried. 5-Phenyl-3-(2-thienylmethylene)-2-furanone (45.3 g), m.p. 141° C., is thereby isolated.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionExtraction
  4. washthe organic phase is washed with a decinormal sodium hydroxide solution, it
  5. dry with materialis dried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-573c30305e5f42898ed3363ad19c34d0
Source dataset
uspto-grants-1989_02
Patent number
US04808599

Reaction notes

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