Acetone → 2,4Dimethyl-3-acetyl-5-isopropyl pyrrole

HRID 1834412Notes

Reaction equation

HRID 1834412 reaction equation
I.[PH2](O)=O.C(OC(=O)C)(=O)C.[CH3:12][C:13]1[NH:14][CH:15]=[C:16]([CH3:21])[C:17]=1[C:18](=[O:20])[CH3:19].[OH-].[NH4+].[CH3:24][C:25]([CH3:27])=O>O>[CH3:12][C:13]1[NH:14][C:15]([CH:25]([CH3:27])[CH3:24])=[C:16]([CH3:21])[C:17]=1[C:18](=[O:20])[CH3:19]

Participants

8

Reactant 6

HCID 180AcetoneHCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 24841Hydrogen iodideHCID 4124402Phosphinic Acid

Product 1

HCID 28252872,4Dimethyl-3-acetyl-5-isopropyl pyrrole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous hydriodic acid (10 ml) and 2 ml of 50% hypophosphorous acid were cooled and stirred while 10 ml of acetic anhydride was slowly added. 2,4-Dimethyl-3-acetyl-pyrrole (548 mg) was dissolved in the solution, 0.6 ml of acetone added, and the mixture was stirred for 1/2 hr. by which time a yellow precipitate had formed and redissolved and the solution had turned yellow; the final temperature was 37° C. It was poured into 100 ml of water and 30 ml of ammonium hydroxide kept at 20° C. The nearly colourless product separated as plates (662 mg, 92%). At 138° C. these changed to cubes which either melted at 165° C. or turned to irregular needles, m.p. 171°-173° C. For analysis, it was recrystallized from aqueous ethanol as colourless plates, m.p. 165.5° C. or 171.5°-173° C.

Workup

  1. additionwas slowly added
  2. additionadded
  3. customby which time a yellow precipitate had formed
  4. dissolutionredissolved
  5. customwas 37° C
  6. customkept at 20° C
  7. customThe nearly colourless product separated as plates (662 mg, 92%)
  8. customAt 138° C.
  9. customFor analysis, it was recrystallized from aqueous ethanol as colourless plates, m.p. 165.5° C. or 171.5°-173° C.

Sources & evidence

ORD record
ord-2cf6779b78c5469e9c1c2f96505c0c56
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

Loading…