Reacción #61381

ord-009a37cd18ae419ead4f70bea018eefc

Ecuación de reacción

CO
methanol
N#CCCCO
3-cyano-1-n-propanol
CCN(CC)CC
triethylamine
ClC(c1ccccc1)(c1ccccc1)c1ccccc1
trityl chloride
N#CCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
desired product
Rendimiento 61.7%
N#CCCCOC(c1ccccc1)(c1ccccc1)c1ccccc1
4-(Trityloxy)butanenitrile
Rendimiento 61.7%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGstirred for 1 h
  2. 2
    ConcentraciónAfter concentration
  3. 3
    Otrothe residue was purified on a column of silica gel

Procedimiento

To a solution of 3-cyano-1-n-propanol (16.85 g, 198 mmol, prepared by method of Blicke, et al., J. Org. Chem. 1961, 26, 3685) in dichloromethane (250 mL) were added triethylamine (80.1 g, 792 mmol) and trityl chloride (82.8 g, 297 mmol) at room temperature and the mixture was stirred for 16 h. To the reaction mixture was added methanol (25 mL) and stirred for 1 h. After concentration, the residue was purified on a column of silica gel using ethyl acetate and hexanes as eluent to give 40 g (61.7%) of the desired product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07429571B2uspto-grants-2008_09