Ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylate → Potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate

HRID 2246380

Reaction equation

HRID 2246380 reaction equation
C[Si](C)(C)[O-].[K+:6].[CH3:7][C:8]1[O:12][C:11]([C:13]([O:15]CC)=[O:14])=[N:10][N:9]=1>CCOCC>[CH3:7][C:8]1[O:12][C:11]([C:13]([O-:15])=[O:14])=[N:10][N:9]=1.[K+:6]

Participants

4

Reactant 2

HCID 13407467Ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylateHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 24820502Potassium 5-methyl-1,3,4-oxadiazole-2-carboxylateYield 109.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a slurry of potassium trimethylsilanolate (411 mg, 3.20 mmol) in ether stirring at rt, was added in one portion ethyl 5-methyl-1,3,4-oxadiazole-2-carboxylate (0.50 g, 3.20 mmol). Immediate precipitation was observed with the color changing from white to off-white. The precipitate was removed by filtration, was washed with ether and dried to give the title compound as an off-white solid (580 mg, quantitative yield). 1H NMR (300 MHz, CDCl3): δ 2.61 (3H, s). 13C NMR (75 MHz, D2O): δ 166.7, 161.3, 159.3, 10.4.

Workup

  1. customImmediate precipitation
  2. customThe precipitate was removed by filtration
  3. washwas washed with ether
  4. customdried

Sources & evidence

ORD record
ord-06921cf071c745c5bbefe14c68b883d3
Source dataset
uspto-grants-2010_03
Patent number
US07687509B2

Linked notes

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