Reacción #83065

ord-586d8aa41bf84e4aa9d16682505234d4

Ecuación de reacción

CC(=O)SC1CSC(CN=[N+]=[N-])C1
product
CC(=O)SC1CSC(CN=[N+]=[N-])C1
Ethanethioic acid S-[5-(azidomethyl)tetrahydro-3-thienyl]ester
C[O-].[Na+]
sodium methoxide
→
[N-]=[N+]=NCC1CC(S)CS1
desired product
Rendimiento 20.7%
[N-]=[N+]=NCC1CC(S)CS1
5-(Azidomethyl)tetrahydro-3-thiophenethiol
Rendimiento 20.7%

Reactantes

CC(=O)SC1CSC(CN=[N+]=[N-])C1
product
CC(=O)SC1CSC(CN=[N+]=[N-])C1
Ethanethioic acid S-[5-(azidomethyl)tetrahydro-3-thienyl]ester
C[O-].[Na+]
sodium methoxide

Reactivos

Ninguno

Disolventes

CO
methyl alcohol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónthe reaction mixture is concentrated in vacuo
  2. 2
    Otrothe residue purified by chromatography (silica gel: 0-5% diethyl ether/hexane)

Procedimiento

A 0° C. solution, under argon, of 0.279 g of product from Example 141 in 3 ml of dry methyl alcohol is treated with 0.35 ml of 4.35M sodium methoxide. After 2 hours, the reaction mixture is concentrated in vacuo and the residue purified by chromatography (silica gel: 0-5% diethyl ether/hexane) to give 0.0465 g of the desired product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05623081uspto-grants-1997_04