Hydrochloric Acid → HCID 20469098, compound

HRID 1388937Notes

Reaction equation

HRID 1388937 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH3:7].[CH3:8][N:9]1[C:13]([C:14](Cl)=[O:15])=[C:12]([CH3:17])[CH:11]=[C:10]1[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].Cl[Sn](Cl)(Cl)Cl.Cl>C(Cl)Cl>[CH3:8][N:9]1[C:13]([C:14]([C:6]2[N:2]([CH3:1])[C:3]([CH3:7])=[CH:4][CH:5]=2)=[O:15])=[C:12]([CH3:17])[CH:11]=[C:10]1[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24287Tin tetrachlorideHCID 38261981,2-dimethylpyrroleHCID 86739290HCID 86739290, compound

Product 1

HCID 20469098HCID 20469098, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Ten mmole (0.95 g) of 1,2-dimethyl-pyrrole and an equivalent amount of t-butyl 1,4-dimethyl-5-chlorocarbonyl-2-pyrrole acetate were dissolved in 10 ml of methylene chloride and stirred at 0° C. under nitrogen atmosphere. Three grams (12 mmole) of SnCl4 in 10 ml methylene chloride was added dropwise and the resulting mixture was stirred at room temperature for three hours followed by pouring into 25 ml 6 N HCl at 0° C. with vigorous stirring. The resulting suspension was extracted three times with 20 ml portions of methylene chloride. The crude extract was column chromatographed and crystallized from ether/hexane to give 1.6 g (50%) of t-butyl 1,4-dimethyl-5-(1,5-dimethylpyrrol-2-oyl)pyrrole-2-acetate.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for three hours
  2. extractionThe resulting suspension was extracted three times with 20 ml portions of methylene chloride
  3. extractionThe crude extract
  4. customchromatographed
  5. customcrystallized from ether/hexane

Sources & evidence

ORD record
ord-16040c41e5e044e198b4460cbf1a3174
Source dataset
uspto-grants-1984_02
Patent number
US04434175

Reaction notes

Loading…