Water → 4-{3-Cyano-4-[2-(2-methoxyethoxy)phenyl]pyrrole-1-yl}-2-methoxymethoxy-benzoic acid ethyl ester

HRID 1516589Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[OH:22])[C:13]([C:23]#[N:24])=[CH:12]2)=[C:7](OC)[C:6]=1[O:27][CH3:28])[CH3:2].[C:30](=[O:33])([O-])[O-].[K+].[K+].BrC[CH2:38][CH2:39][O:40][CH3:41].O>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:29])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[O:22][CH2:38][CH2:39][O:40][CH3:41])[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][C:6]=1[O:27][CH2:28][O:33][CH3:30])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-[4-(2-hydroxyphenyl)-3-cyanopyrrole-1-yl]-2-methoxy-methoxy benzoic acid ethyl ester (0.12 g) and potassium carbonate (0.10 g) in N,N-dimethylformamide (1 mL) was added 1-bromo-3-methoxy-propane (0.092 g), and this mixture was stirred at 70° C. for 18 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (0.12 g).

Workup

extractionthis mixture was extracted with ethyl acetate
washThis organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-fbc04eef3fb84b69ae3aada9eb5a7c2a
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08227500B2

Reaction notes

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