Ketone, 2,4-dimethylpyrrol-3-yl methyl → HCID 653478, compound

HRID 1834420Notes

Reaction equation

HRID 1834420 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].[I-].[PH4+].[CH3:13][CH:14]1OC(C)OC(C)O1>I>[CH3:1][C:2]1[NH:3][C:4]([CH2:13][CH3:14])=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methylHCID 31264ParaldehydeHCID 166618Phosphonium iodide ((PH4)I)

Product 1

HCID 653478HCID 653478, compound

Reagents, catalysts & solvents 1

HCID 24841Hydrogen iodideSolvent

Procedure

A solution of 2,4-dimethyl-3-acetyl-pyrrole (548 mg) in 10 ml of aqueous hydriodic acid containing a little solid phosphonium iodide was cooled in an ice-salt bath. Paraldehyde (0.35 ml) was added and the solution was stirred for 41/2 hrs. without further cooling. The solution was then added to 100 ml of ice water to precipitate the light brown product (385 mg, 58%), m.p. 153°-160° C. For analysis, it was sublimed in vacuo then recrystallized from ether (thimble) as grey needles, m.p. 163° C. after changing to plates at 140°. Anal. Calc. for C10H15O: C; 72.69, H, 9.15; N, 8.48. Found: C, 72.67; H, 8.88; N, 8.69.

Workup

  1. customto precipitate the light brown product (385 mg, 58%), m.p. 153°-160° C
  2. customthen recrystallized from ether (thimble) as grey needles, m.p. 163° C.
  3. customafter changing to plates at 140°

Sources & evidence

ORD record
ord-7e551574c6084e63bcf58bcecca18156
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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