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

HRID 2375375Notes

Reaction equation

HRID 2375375 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N:11]1[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]1[CH3:17].[C:18](OC(=O)C)(=[O:20])[CH3:19].I>>[C:18]([C:13]1[CH:14]=[C:15]([CH3:16])[N:11]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])[C:12]=1[CH3:17])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 24841Hydrogen iodideHCID 39247986HCID 39247986, compound

Product 1

HCID 393723951-[1-(2,4-Dimethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Procedure

Utilizing the general procedure outlined in EXAMPLE 1, 1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (2.31 g, 10 mmol), acetic anhydride (5 mL), and hydriodic acid (0.13 mL, 1.7 mmol) reacted to give 3-acetyl-1-(2,4dimethoxyphenyl)-2,5-dimethylpyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.02 (dd, 1H), 6.59 (d, 1H), 6.55 (dd, 1H), 6.32 (s, 1H), 3.90 (s, 3H), 3.76 (s, 3H), 2.42 (s, 3H), 2.25 (s, 3H), 1.93 (s, 3H); MS (ESI) 274 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-3ddfa6683318405faaa198c51ef13301
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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