Methyl 2-furoate → Potassium furan-2-carboxylate

HRID 3944

Reaction equation

HRID 3944 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]C)=[O:7].C[Si](C)(C)[O-].[K+:15]>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O-:8])=[O:7].[K+:15]

Participants

4

Reactant 2

HCID 11902Methyl 2-furoateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 19205452Potassium furan-2-carboxylateYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure of Example 1 was followed using methyl 2-furoate (2.52 g, 20 mmol), potassium trimethylsilanolate (2.56 g, 20 mmol), dry tetrahydrofuran (50 mL), and a 5 h reaction time. Potassium 2-furoate (2.72 g, 90% yield) was isolated as a light brown solid: 1H NMR (D2O, DSS) δ 6.55 (m, Ar--H, 1H), 7.0 (m, Ar--H, 1H) and 7.6 ppm (m, Ar--H, 1H). Anal. Calcd. for C5H3KO3 : C, 39.99; H, 2.01; K, 26.04. Found: C, 37.22, 37.41, 40.26; H, 2.33, 2.19, 2.34; K, 26.22.

Workup

  1. customa 5 h reaction time

Sources & evidence

ORD record
ord-a2a03d9eacb9456cbafbe3371aa2289a
Source dataset
uspto-grants-1988_02
Patent number
US04723016

Linked notes

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