Dimethylformamide → 1-(5-Formylthiophen-2-yl)cyclopent-3ene carboxylic acid ethyl ester

HRID 481388Notes

Reaction equation

HRID 481388 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([O:8][C:9]([C:11]1([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[CH3:7].CN([CH:24]=[O:25])C>>[CH2:6]([O:8][C:9]([C:11]1([C:16]2[S:17][C:18]([CH:24]=[O:25])=[CH:19][CH:20]=2)[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[CH3:7]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 539343521-Thiophen-2-yl-cyclopent-3-ene carboxylic acid ethyl ester2×

Product 1

HCID 542933021-(5-Formylthiophen-2-yl)cyclopent-3ene carboxylic acid ethyl ester

Conditions

Temperature
105 °C

Procedure

POCl3 (275 mg, 1.8 mmol) was added to 1 ml DMF at ambient temperature and stirred for 30 minutes. The product of Step 1, above (2) (208 mg, 0.93 mmol), was dissolved in 1 ml DMF, added to the reaction mixture and stirred for 1 hour at ambient temperature. The reaction mixture was heated to 105° C. for 3 hours, cooled to ambient temperature, quenched with saturated sodium acetate solution and extracted (2×10 ml, EtOAc). The organics were washed with brine and dried over MgSO4, filtered and concentrated to yield the title compound (3).

Workup

  1. additionadded to the reaction mixture
  2. stirringstirred for 1 hour at ambient temperature
  3. temperaturecooled to ambient temperature
  4. customquenched with saturated sodium acetate solution
  5. extractionextracted (2×10 ml, EtOAc)
  6. washThe organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5110a2e79833499798fe2035b0158e41
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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