Thiophene → Cyclopentyl-2-thienylmethanone

HRID 235094Notes

Reaction equation

HRID 235094 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(O)=O)CCCC1.S(Cl)(Cl)=O.[S:21]1[CH:25]=[CH:24][CH:23]=[CH:22]1.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[CH:1]1([C:6]([C:22]2[S:21][CH:25]=[CH:24][CH:23]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 8030ThiopheneHCID 18840Cyclopentanecarboxylic acidHCID 24287Tin tetrachlorideHCID 24386Thionyl ChlorideHCID 78284Cyclopentanecarbonyl chloride

Product 1

HCID 10219686Cyclopentyl-2-thienylmethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Cyclopentanecarboxylic acid chloride, prepared from 100 mmol cyclopentanecarboxylic acid and 120 mmol of thionyl chloride, was dissolved in 100 mL of methylene chloride, and the solution was cooled in an ice bath. Thiophene (13.4 mL, 100 mmol) and SnCl4 (25 mL of a 1M solution in methylene chloride) were added. The reaction was warmed to room temperature and stirred for 72 hours. The reaction was quenched with 1 N HCl, and the mixture was extracted with three portions of methylene chloride. The organic extract was washed with satd aqueous NaHCO3, was dried over MgSO4, and filtered through a pad of silica gel. The solvent was removed by rotary evaporation to give 12.28 g of crude product, which was used without further purification.

Workup

  1. temperaturethe solution was cooled in an ice bath
  2. customThe reaction was quenched with 1 N HCl
  3. extractionthe mixture was extracted with three portions of methylene chloride
  4. extractionThe organic extract
  5. washwas washed with satd aqueous NaHCO3
  6. dry with materialwas dried over MgSO4
  7. filtrationfiltered through a pad of silica gel
  8. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-95d166eb65f54d5d9d07923bb23d65ab
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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