Malonic Acid → HCID 70388328, compound

HRID 2291611Notes

Reaction equation

HRID 2291611 reaction equation
[C:1]1([CH:7]2[C:12]3[CH:13]=[C:14]([CH:16]=O)[S:15][C:11]=3[C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[O:8]2)[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1.C(O)(=O)[CH2:23][C:24]([OH:26])=[O:25].N1C=CC=CC=1.N1CCCCC1>O>[C:1]1([CH:7]2[C:12]3[CH:13]=[C:14]([CH:16]=[CH:23][C:24]([OH:26])=[O:25])[S:15][C:11]=3[C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[O:8]2)[CH:6]=[CH:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 867Malonic AcidHCID 1049PyridineHCID 8082PiperidineHCID 86742663HCID 86742663, compound

Product 1

HCID 70388328HCID 70388328, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 17.6 g 4H-4-phenyl-thieno[3,2-c][1]benzopyran-2-carboxaldehyde, 12.5 g malonic acid and 24 ml pyridine is slightly heated until a clear solution is obtained. Subsequently, 1 ml piperidine is added and the solution slowly heated to reflux. After 3 h reflux, the solution is cooled and poured into water. After acidification with hydrochloric acid, the crude product is filtered off, dried, recrystallized from ethyl acetate and dried in vacuo. Pure 3-(4H-4-phenyl-thieno[3,2-c][1]benzopyran-2yl)propenoic acid is obtained; m.p. 235° C. (decomposition).

Workup

  1. customis obtained
  2. temperaturethe solution slowly heated to reflux
  3. temperatureAfter 3 h reflux
  4. temperaturethe solution is cooled
  5. filtrationAfter acidification with hydrochloric acid, the crude product is filtered off
  6. customdried
  7. customrecrystallized from ethyl acetate
  8. customdried in vacuo

Sources & evidence

ORD record
ord-9d4a5c48f3b345048231511bf79a529a
Source dataset
uspto-grants-1989_01
Patent number
US04797414

Reaction notes

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