Diethyl Ether → Methyl 5-methyl-2-thiophenecarboxylate

HRID 1442524Notes

Reaction equation

HRID 1442524 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][CH:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].CI.C(OCC)C>CN(C)C=O>[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 747135-Methylthiophene-2-carboxylic acid

Product 1

HCID 580756Methyl 5-methyl-2-thiophenecarboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-methylthiophene-2-carboxylic acid (40.3 g, 282 mmol) in N,N-dimethylformamide (500 ml) were added potassium carbonate (43 g, 310 mmol) and methyl iodide (19.3 ml, 310 mmol). After stirring at room temperature for 4 hr, diethyl ether (1.0 L) was added, and the organic layer was washed successively with water (500 ml×3) and saturated brine (200 ml) and dried over magnesium sulfate. After filtration and concentration, methyl 5-methylthiophene-2-carboxylate (40.8 g, yield 93%) was obtained.

Workup

  1. washthe organic layer was washed successively with water (500 ml×3) and saturated brine (200 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-cb53c07a4278464fba772991f83d06fe
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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