Reacción #595353

ord-6b7e7f26f04c47f5abd74893c73ab4d4

Ecuación de reacción

COC(=O)c1oc(-c2ccc(Cl)cc2)nc1CO
compound
COC(=O)c1oc(-c2ccc(Cl)cc2)nc1CO
Methyl 2-(4-chlorophenyl)-4-(hydroxymethyl)-1,3-oxazole-5-carboxylate
O=S(Cl)Cl
thionyl chloride
COC(=O)c1oc(-c2ccc(Cl)cc2)nc1CCl
Methyl 4-(chloromethyl)-2-(4-chlorophenyl)-1,3-oxazole-5-carboxylate

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe excess thionyl chloride is removed under reduced pressure
  2. 2
    LavadoThe mixture is washed once with 2 ml of sat. aqueous sodium bicarbonate solution
  3. 3
    SecadoThe organic phase is dried over magnesium sulfate
  4. 4
    Otrothe solvent is removed under reduced pressure
  5. 5
    OtroThe product obtained
  6. 6
    Otrois used without further purification in the subsequent reactions

Procedimiento

100 mg (0.43 mmol) of the compound from Example 44A, together with 0.24 ml (3.24 mmol) of thionyl chloride, are stirred at RT for 8 h. The excess thionyl chloride is removed under reduced pressure and the residue is taken up in about 5 ml of ethyl acetate. The mixture is washed once with 2 ml of sat. aqueous sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The product obtained is used without further purification in the subsequent reactions.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095582B2uspto-grants-2015_08