Methyl 4-chloroformylbutyrate → HCID 69275406, compound

HRID 2375371Notes

Reaction equation

HRID 2375371 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[CH:12][CH:11]=2)[C:5]=1[CH3:19])(=[O:3])[CH3:2].Cl[C:21](=[O:29])[CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>>[CH3:28][O:27][C:25](=[O:26])[CH2:24][CH2:23][CH2:22][C:21]([C:8]1[C:4]([C:1](=[O:3])[CH3:2])=[C:5]([CH3:19])[N:6]([C:10]2[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH3:18])=[CH:14][CH:15]=2)[C:7]=1[CH3:9])=[O:29]

Participants

3

Reactant 2

HCID 73916Methyl 4-chloroformylbutyrateHCID 201096531-[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

Product 1

HCID 69275406HCID 69275406, compound

Procedure

Utilizing the general procedure outlined in EXAMPLE 1, 3-acetyl-2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole (771 mg, 3.0 mmol) and methyl 5-chloro-5-oxovalerate (0.63 mL, 4.5 mmol) reacted to give 5-[4-acetyl-2,5-dimethyl-1-(4-ethoxyphenyl)-1H-pyrrol-3-yl]-5-oxo-pentanoic acid methyl ester as a white solid: 1H NMR (CDCl3, 500 MHz) δ 7.05 (d, 2H), 6.98 (d, 2H), 4.08 (q, 2H), 3.65 (s, 3H), 2.75 (t, 2H), 2.41 (s, 3H), 2.40 (t, 2H), 2.11 (s, 3H), 2.01 (s, 3H), 2.00 (quintet, 2H), 1.45 (t, 3H); MS (ESI) 386 (M+H)+.

Workup

  1. customreacted

Sources & evidence

ORD record
ord-0c182abfd65f4f018e73d0a0cc5faad7
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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