Cyclopentanone → HCID 20373154, compound

HRID 1834432Notes

Reaction equation

HRID 1834432 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8].[C:11]1(=O)[CH2:15][CH2:14][CH2:13][CH2:12]1>I.C(OC(=O)C)(=O)C.[PH2](O)=O>[CH3:1][C:2]1[NH:3][C:4]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[C:5]([CH3:10])[C:6]=1[C:7](=[O:9])[CH3:8]

Participants

6

Reactant 2

HCID 8452CyclopentanoneHCID 15163Ketone, 2,4-dimethylpyrrol-3-yl methyl

Product 1

HCID 20373154HCID 20373154, compound

Reagents, catalysts & solvents 3

HCID 7918Acetic AnhydrideSolventHCID 24841Hydrogen iodideSolventHCID 4124402Phosphinic AcidSolvent

Procedure

2,4-Dimethyl-3-acetyl-pyrrole (0.548 g) was dissolved in a mixture of hydriodic acid (10 ml), acetic anhydride (10 ml) and hypophosphorous acid (2 ml). The solution was stirred at 40° while cyclopentanone (1.5 ml) was added in three portions over 3/4 hr. After stirring an additional 1/2 hr., the solution was poured into ice water (125 ml) and the pale yellow product (95%), m.p. 161.5°-163.5° after changing to prisms at ca 140°, separated. For analysis it was recrystallized successively from hexane, from aqueous methanol and again from n-hexane as pale pink prisms m.p. 167.5°-168° (lit20), 164.5°-165.5°). Anal. Calc. for C13H19NO: C, 76.05, H, 9.33; N, 6.82. Found: C, 76.12; H, 9.21; N, 6.65.

Workup

  1. additionwas added in three portions over 3/4 hr
  2. customafter changing to prisms at ca 140°
  3. customseparated
  4. customFor analysis it was recrystallized successively from hexane, from aqueous methanol and again from n-hexane as pale pink prisms m.p. 167.5°-168° (lit20), 164.5°-165.5°)

Sources & evidence

ORD record
ord-fcfa0f6103054ed89661dd7ee9973a00
Source dataset
uspto-grants-1978_01
Patent number
US04070366

Reaction notes

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