Ethyl Thioglycolate → Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

HRID 9638

Reaction equation

HRID 9638 reaction equation
[H-].[Na+].F[P-](F)(F)(F)(F)F.Cl[C:11]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=1)=[CH:12][C:13](=[N+](C)C)[CH3:14].[C:28]([O:32][CH2:33][CH3:34])(=[O:31])[CH2:29][SH:30]>C(O)C>[CH3:14][C:13]1[CH:12]=[C:11]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[S:30][C:29]=1[C:28]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 86593913N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate2×

Product 1

HCID 15946279Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.528 g) was added to dry ethanol (20 ml), N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate (intermediate 34, 2.8 g) was added followed by ethyl thioglycolate (0.79 g) and the mixture heated at 110° C. for 2 hours under nitrogen. The cooled mixture was concentrated in vacuo and the residue partitioned between water and diethyl ether. The organic layer was collected, dried over magnesium sulphate and concentrated to give the title compound as a brown solid.

Workup

  1. additionwas added
  2. concentrationThe cooled mixture was concentrated in vacuo
  3. customthe residue partitioned between water and diethyl ether
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6ea3ca517d7342f6ac2c54fa506a38d2
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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