Reacción #1515069

Ecuación de reacción

4-(adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)-benzonitrile

triethylsilane

trifluoroacetic acid

→

4-(adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile

Disolventes

methylene chloride

sodium hydroxide

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with methylene chloride (3×50 mL)
2. 2
   LavadoThe combined organic layers were washed with brine (50 mL)
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue was purified by column chromatography
7. 7
   Lavadoeluting with a 5% to 10% gradient of ethyl acetate in hexanes

Procedimiento

To a cooled (0° C.) stirred solution of 4-(adamantan-1-ylmethoxy)-3-(1-hydroxycyclobutyl)-benzonitrile (1.00 g, 2.96 mmol) in methylene chloride (30 mL) was added triethylsilane (2.4 mL, 14.80 mmol) followed by trifluoroacetic acid (2.3 mL, 29.60 mmol). The reaction mixture was stirred at 0° C. for 1.5 h and diluted with 1M aqueous sodium hydroxide solution (30 mL). The mixture was extracted with methylene chloride (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluting with a 5% to 10% gradient of ethyl acetate in hexanes to afford 4-(adamantan-1-ylmethoxy)-3-cyclobutylbenzonitrile as colorless solid in quantitative yield (0.95 g): MS (ES+) m/z 322.2 (M+1);

Fuente