Reacción #833553

Ecuación de reacción

butyl lithium

2-methyl-5,6,7,8-tetrahydro-naphthalene-3-sulfonic acid methylamide

CO2

HCl

→

3-(N-methyl-sulfamoyl)-5,6,7,8-tetrahydro-naphthalene-2-acetic acid

Disolventes

hexane

tetrahydrofuran

water

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto come to room temperature
2. 2
   Extracciónextracted with CH2Cl2
3. 3
   LavadoThe CH2Cl2 solution was washed
4. 4
   Otrodried
5. 5
   Concentraciónconcentrated
6. 6
   OtroRecrystallization from ether/petroleum ether

Procedimiento

100 mL of a 1.5 molare (150 mmol) butyl lithium in hexane were added to a solution of 18 g (75 mmol) 2-methyl-5,6,7,8-tetrahydro-naphthalene-3-sulfonic acid methylamide in 200 mL tetrahydrofuran at −20° C. The resulting mixture was allowed to come to room temperature and was poured onto a mixture of ether and solid CO2. After addition of water the resulting mixture was acidified with dilute HCl and then extracted with CH2Cl2. The CH2Cl2 solution was washed, dried and concentrated. Recrystallization from ether/petroleum ether gave 15.8 g 3-(N-methyl-sulfamoyl)-5,6,7,8-tetrahydro-naphthalene-2-acetic acid (melting point: 153-155° C.).

Fuente