Ethyl Bromide → 1-[1-(4-Ethoxy-2-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

HRID 2375383Notes

Reaction equation

[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][C:11]=2[O:17][CH3:18])[C:5]=1[CH3:19])(=[O:3])[CH3:2].Br[CH2:21][CH3:22]>>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:21][CH3:22])=[CH:12][C:11]=2[O:17][CH3:18])[C:5]=1[CH3:19])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 6332Ethyl Bromide

HCID 69275389HCID 69275389, compound

Product 1

HCID 692755891-[1-(4-Ethoxy-2-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Procedure

Using the general procedure outlined in EXAMPLE 1, 3-acetyl-2,5-dimethyl-1-(4-hydroxy-2-methoxyphenyl)pyrrole (1.37 g, 5.3 mmol) and an excess of bromoethane (2.0 mL) reacted to give 3-acetyl-2,5-dimethyl-1-(4-ethoxy-2-methoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 6.99 (d, 1H), 6.59 (d, 1H), 6.53 (dd, 1H), 6.31 (s, 1H), 4.08 (q, 2H), 3.74 (s, 3H), 2.41 (s, 3H), 2.25 (s, 3H), 1.93 (s, 3H), 1.46 (t, 3H); MS (ESI) 288 (M+H)+.

Sources & evidence

ORD record: ord-9bedc9adcd6f40c0b169f208ff421f0b
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465730B2

Reaction notes

Loading…