Ethanol → Ethyl 5-methyl-2-thiophenecarboxylate

HRID 1168541Notes

Reaction equation

HRID 1168541 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-thiophenecaboxylic 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-2cb2c605151c479ba39cab1a6979e917
Source dataset
uspto-grants-2003_09
Patent number
US06624188B1

Reaction notes

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