Dimethylformamide → Ethyl 5-(tetradecyloxy)thiophene-2-carboxylate

HRID 596656Notes

Reaction equation

HRID 596656 reaction equation
[CH2:1]([O:15][C:16]1[S:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[CH2:35](I)[CH3:36]>O>[CH2:35]([O:22][C:21]([C:19]1[S:20][C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:17][CH:18]=1)=[O:23])[CH3:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 123615105-(Tetradecyloxy)thiophene-2-carboxylic acid

Product 1

HCID 53699008Ethyl 5-(tetradecyloxy)thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 10.6 g (0.031 mole) of 5-tetradecyloxy-2-thiophene carboxylic acid, 4.3 g (0.034 mole) of potassium carbonate, and dimethylformamide is stirred at room temperature after which 15.6 g (0.10 mole) of ethyl iodide is added. The mixture is heated at 50° C with stirring overnight and poured into water and extracted with the ether. The ether layer is washed with water and salt water and then dried over sodium sulfate, filtered, and the ether is distilled off to give 5-tetradecyloxy-2-thiophenecarboxylic acid ethyl ester.

Workup

  1. additionis added
  2. extractionextracted with the ether
  3. washThe ether layer is washed with water and salt water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. distillationthe ether is distilled off

Sources & evidence

ORD record
ord-a96bc2731f744ef18b6583636f8d4aca
Source dataset
uspto-grants-1977_03
Patent number
US04011333

Reaction notes

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