Ethanol → Ethyl 5-methyl-2-thiophenecarboxylate

HRID 275031Notes

Reaction equation

HRID 275031 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCC[CH2:2]1.[CH3:16][C:17]1[S:21][C:20]([C:22]([OH:24])=[O:23])=[CH:19][CH:18]=1.C(O)C.CN(C1C=CC=CN=1)C>ClCCl>[CH3:16][C:17]1[S:21][C:20]([C:22]([O:24][CH2:1][CH3:2])=[O:23])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 747135-Methylthiophene-2-carboxylic acid

Product 1

HCID 11019293Ethyl 5-methyl-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 15.9 g (77.4 mmol) of 1,3-dicyclohexylcarbodiimide in 40 mL dichloromethane was added 10 g (70.3 mmol) of 5-methyl-2-thiophenecarboxylic acid and 4.85 g (105.5 mmol) of anhydrous ethanol. 0.86 g of dimethylaminopyridine was then added and the suspension stirred at room temperature for 20 hours. The resulting white precipitate was removed by filtration. The filtrate was washed with water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by bulb-to-bulb distillation (bp=95° C., 3 mm Hg) to give the title compound as a clear, pale yellow oil.

Workup

  1. customThe resulting white precipitate was removed by filtration
  2. washThe filtrate was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationThe residue was purified by bulb-to-bulb distillation (bp=95° C., 3 mm Hg)

Sources & evidence

ORD record
ord-e7d53b94eab4416eb209b099e6da4ad6
Source dataset
uspto-grants-1995_02
Patent number
US05391753

Reaction notes

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