Reacción #417927

ord-cda7f11bc0f547278685aaea9a341ae8

Ecuación de reacción

C1CCCCC1.CCOC(C)=O
ethylacetate cyclohexane
CC(=O)SCc1ccccc1C(F)(F)F
thioacetic acid S-(2-trifluoromethyl-benzyl)ester
CO
methanol
COC(=O)c1ncccc1CBr
3-Bromomethyl-pyridine-2-carboxylic acid methyl ester
COC(=O)c1ncccc1CSCc1ccccc1C(F)(F)F
colorless crystals
Rendimiento 100.0%
COC(=O)c1ncccc1CSCc1ccccc1C(F)(F)F
3-(2-Trifluoromethyl-benzylsulfanylmethyl)-pyridine-2-carboxylic acid methyl ester
Rendimiento 100.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturaafter refluxing for 150 min the solution
  2. 2
    Extracciónextracted with ethylacetate
  3. 3
    Secadothe organic phase dried with sodium sulfate
  4. 4
    Concentraciónconcentrated

Procedimiento

To a solution of thioacetic acid S-(2-trifluoromethyl-benzyl)ester (10.2 g, 37.5 mmol) in methanol (130 ml) potassium carbonate (5.18 g, 37.5 mmol) was added at room temperature and it was stirred for 30 min. 3-Bromomethyl-pyridine-2-carboxylic acid methyl ester (4.40 g, 18.7 mmol) was added and after refluxing for 150 min the solution was diluted with water, extracted with ethylacetate, the organic phase dried with sodium sulfate and concentrated. Chromatography over silica with ethylacetate/cyclohexane gave 7.82 g colorless crystals (18.7 mmol).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08877683B2uspto-grants-2014_11