Potassium Hydroxide → 5-Ethylthiophene-3-carboxylic acid

HRID 1809078Notes

Reaction equation

HRID 1809078 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][CH3:14])[S:10][CH:9]=1)=[O:7])C>O>[CH2:13]([C:11]1[S:10][CH:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=1)[CH3:14]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12588559Ethyl 5-ethylthiophene-3-carboxylate

Product 1

HCID 35615485-Ethylthiophene-3-carboxylic acidYield 81.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium hydroxide (1.02 g, 18.3 mmol) in water (3 mL) was added to a solution of 5-ethyl-thiophene-3-carboxylic acid ethyl ester (6.1 mmol) in IMS (9 mL). The reaction was stirred for 1 hour then partitioned between diethyl ether and water. The aqueous layer was acidified to pH 7 with concentrated hydrochloric acid and extracted with diethyl ether. The organic solution was dried over magnesium sulphate, filtered and the solvent removed to give the title compound (0.78 g). 1H NMR (400 MHz, CHCl3-d): δ 8.0 (s, 1H), 7.2 (s, 1H), 2.8 (q, 2H), 1.3 (t, 3H).

Workup

  1. customthen partitioned between diethyl ether and water
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic solution was dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-97454f18ee64441fb97cf922caab221b
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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