Acetic Acid → 1-(1-Propen-2-yl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole

HRID 1769088Notes

Reaction equation

HRID 1769088 reaction equation
[Cl-].[Ca+2].[Cl-].C(O)(=O)C.O[C:9]([C:12]1[S:13][CH:14]=[C:15]2[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C:16]=12)([CH3:11])[CH3:10]>C(Cl)(Cl)Cl>[CH2:10]=[C:9]([C:12]1[S:13][CH:14]=[C:15]2[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][C:16]=12)[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5284359Calcium ChlorideHCID 18947031HCID 18947031, compound

Product 1

HCID 189470701-(1-Propen-2-yl)-5-(1,1-dimethylethoxy)carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrroleYield 102.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5 g of calcium chloride and 0.17 ml (3 mmol) of acetic acid are added to a solution of 0.81 g (2.86 mmol) of 1-(2-hydroxy-2-propyl)-5-(1,1-dimethyl-ethoxy) carbonyl-5,6-dihydro-4H-thieno[3,4-c]pyrrole in 60 ml of chloroform. The mixture is heated at reflux for 24 hours, filtered, washed with a 5% sodium bicarbonate solution, then dried over sodium sulphate and evaporated to dryness. 0.78 g of an oily product is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 hours
  3. filtrationfiltered
  4. washwashed with a 5% sodium bicarbonate solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-7950159fa4d64dec9c7960ca8d1f4f5b
Source dataset
uspto-grants-1995_01
Patent number
US05380742

Reaction notes

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