Hydrochloric Acid → (E)-8-[3-(3-thienyl)phenyl]-3-oxo-7-octenoic acid methyl ester

HRID 1757265Notes

Reaction equation

HRID 1757265 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8](/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH2:16][C:17]#N)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[CH3:19][O:20][C:21](=[O:24])[CH2:22]Br.Cl.[O:26]1CCCC1>[Zn]>[CH3:19][O:20][C:21](=[O:24])[CH2:22][C:17](=[O:26])[CH2:16][CH2:15][CH2:14]/[CH:13]=[CH:12]/[C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 60984Methyl bromoacetateHCID 19390157HCID 19390157, compound

Product 1

HCID 67787886(E)-8-[3-(3-thienyl)phenyl]-3-oxo-7-octenoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

3.64 g of the above nitrile compound and 3.92 g of activated zinc powder are added to 50 ml of tetrahydrofuran, 4.54 ml of bromoacetic acid methyl ester is added dropwise to this mixture over a period of 1 hour under reflux with heating and stirring, and the mixture is further stirred under reflux for 1 hour. 100 ml of 10% hydrochloric acid is added to the reaction solution, the mixture is stirred at room temperature for 30 minutes, tetrahydrofuran is distilled off under reduced pressure, and methylene chloride is added to the residual solution for extraction. The extract is washed with saturated saline and post-treated in a conventional manner, and the product is purified by silica gel column chromatography [Wako gel C-200, 100 g; hexane/ethyl acetate=4/1] to obtain 2.33 g of (E)-8-[3-(3-thienyl)phenyl]-3-oxo-7-octenoic acid methyl ester as colorless oil.

Workup

  1. additionis added dropwise to this mixture over a period of 1 hour
  2. temperatureunder reflux
  3. temperaturewith heating
  4. stirringthe mixture is further stirred
  5. temperatureunder reflux for 1 hour
  6. stirringthe mixture is stirred at room temperature for 30 minutes
  7. distillationtetrahydrofuran is distilled off under reduced pressure, and methylene chloride
  8. additionis added to the residual solution for extraction
  9. washThe extract is washed with saturated saline
  10. additionpost-treated in a conventional manner
  11. customthe product is purified by silica gel column chromatography [Wako gel C-200, 100 g; hexane/ethyl acetate=4/1]

Sources & evidence

ORD record
ord-abe73587e623483d9a9b30b5e5f39667
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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