Reacción #320615

Ecuación de reacción

1-chloromethyl-2-methylnaphthalene

trimethylphosphite

→

solid

Rendimiento 59.1%

(2-Methyl-1-naphthalenylmethyl)phosphonic acid, dimethyl ester

Rendimiento 59.1%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux temperature for 48 hours
2. 2
   OtroExcess trimethylphosphite is removed under reduced pressure
3. 3
   Otrogiving a yellow oil which
4. 4
   Otrois chromatographed over silica gel (40-63 μ, 400 g, 50 mL fractions)
5. 5
   Lavadofor elution of the column
6. 6
   Concentraciónafter concentration

Procedimiento

A solution of 1-chloromethyl-2-methylnaphthalene (9.50 g, 0.050M) in trimethylphosphite (15 mL, 15.8 g, 0.13 M) is heated at reflux temperature for 48 hours. Excess trimethylphosphite is removed under reduced pressure, giving a yellow oil which is chromatographed over silica gel (40-63 μ, 400 g, 50 mL fractions) using ethyl acetate for elution of the column. Fractions 18-21 are pooled and after concentration gave a white solid (7.78 g). Recrystallization from ether-pentane gave title compound (6.94 g) as colorless crystals, mp 54°-57° C.

Fuente