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

HRID 1834411Notes

Reaction equation

HRID 1834411 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].[CH3:11][C:12]([CH3:14])=O.O>Br.C(O)(=O)C>[CH3:1][C:2]1[NH:3][C:4]([CH:12]([CH3:14])[CH3:11])=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

6

Reactant 3

HCID 180AcetoneHCID 962WaterHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methyl

Product 1

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

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Conditions

Temperature
30 °C

Procedure

Anhydrous stannous bromide (5g) was stirred to solution in 20 ml of hydrogen bromide in acetic acid (30-32 %). 2,4-Dimethyl-3-acetyl-pyrrole (548 mg) was added and the mixture was warmed to dissolve this, then cooled to 30° C. Acetone(0.6 ml) was added and the solution was stirred at 35° C. for 21/2 hrs then poured into water at 10° C. The product was separated and washed with dilute hydrochloric acid then with water. It formed colourless micro-prisms (549 mg. 77%), m.p. 166°-167° C. or 173-174.5° C. after changing to cubes at about 136° C. For analysis it was recrystallized from aqueous ethanol as prismatic rods, m.p. 172° C.

Workup

  1. temperaturethe mixture was warmed
  2. dissolutionto dissolve this,
  3. customThe product was separated
  4. washwashed with dilute hydrochloric acid
  5. customIt formed colourless micro-prisms (549 mg. 77%), m.p. 166°-167° C. or 173-174.5° C.
  6. customafter changing to cubes at about 136° C
  7. customFor analysis it was recrystallized from aqueous ethanol as prismatic rods, m.p. 172° C.

Sources & evidence

ORD record
ord-fd15fbc6001b447b9e1d033854dbe994
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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