Acetic Anhydride → 1-[1-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

HRID 2375378Notes

Reaction equation

HRID 2375378 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][C:9]=2[CH3:17])[C:4]([CH3:7])=[CH:5][CH:6]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19].I>>[C:18]([C:5]1[CH:6]=[C:2]([CH3:1])[N:3]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][C:9]=2[CH3:17])[C:4]=1[CH3:7])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 692752351-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrole

Product 1

HCID 692752741-[1-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Procedure

Utilizing the general procedure outlined in EXAMPLE 1, 2,5-dimethyl-1-(4-ethoxy-2-methylphenyl)pyrrole (2.29 g, 10 mmol), acetic anhydride (5 mL), and hydriodic acid (0.13 mL, 1.7 mmol) reacted to give 3-acetyl-2,5-dimethyl-1-(4-ethoxy-2-methylphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 6.99 (d, 1H), 6.85 (d, 1H), 6.79 (dd, 1H), 6.32 (s, 1H), 4.06 (q, 2H), 2.42 (s, 3H), 2.22 (s, 3H), 1.89 (s, 3H), 1.88 (s, 3H), 1.44 (t, 3H); MS (ESI) 272 (M +H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-4ece2c5b494a4056bda576bfbeb8870d
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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