2,2-Diethoxytetrahydrofuran → 3,5-Dimethoxy-4-(pyrrol-1-yl)-benzoic acid methyl ester

HRID 542953

Reaction equation

C(O[C:4]1(OCC)[CH2:8][CH2:7][CH2:6]O1)C.[CH3:12][O:13][C:14](=[O:26])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([NH2:23])=[C:17]([O:24][CH3:25])[CH:16]=1>C(O)(=O)C>[CH3:12][O:13][C:14](=[O:26])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([N:23]2[CH:4]=[CH:8][CH:7]=[CH:6]2)=[C:17]([O:24][CH3:25])[CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 9 g. of diethoxy-tetrahydrofuran and 5 ml. of glacial acetic acid was added dropwise at room temperature to a solution of 10.5 g of 4-amino-3,5-dimethoxy-benzoic acid methyl ester in 50 ml. of glacial acetic acid with stirring. The mixture was stirred at 100° C. for an additional 30 minutes, cooled with ice, filtered under vacuum, dried and recrystallized from cyclohexane, whereby there was obtained 3,5-dimethoxy-4-(pyrrol-1-yl)-benzoic acid methyl ester having a melting point of 145°-146° C.

Workup

additionA mixture of 9 g
temperaturecooled with ice
filtrationfiltered under vacuum
customdried
customrecrystallized from cyclohexane

Sources & evidence

ORD record: ord-7b612eb1b3f143e89167538b7e61baea
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04659818

Linked notes

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