Reacción #83115

Ecuación de reacción

2-adamantanol

bis(trichloromethyl)carbonate

pyridine

→

2-Adamantylchloroformate

Disolventes

CH2Cl2

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was removed in vacuo at 30° C.
2. 2
   workup.STIRRINGstirred for 10 minutes
3. 3
   FiltraciónThe pyridinium hydrochloride precipitate was filtered off
4. 4
   Otrothe solvent removed in vacuo at 30° C.
5. 5
   Otroto give an oil which

Procedimiento

To a stirred solution of 2-adamantanol (0.912 g, 6 mmol) in dry CH2Cl2 (15 mL) was added bis(trichloromethyl)carbonate (0.653 g), pyridine in dry CH2Cl2 (10 mL) at 0° C. The reaction mixture was warmed to room temperature and stirred for two hours. The solvent was removed in vacuo at 30° C., taken up in ethyl acetate (30 mL) and stirred for 10 minutes. The pyridinium hydrochloride precipitate was filtered off and the solvent removed in vacuo at 30° C., to give an oil which solidified upon standing (1.29 g, 100%). IR (film) 1778 cm-1 ; NMR (CDCl3) δ1.55-1.65 (2H, m), 1.70-1.80 (4H, m), 1.85-1.95 (4H, m), 2.00-2.10 (2H, m), 2.15-2.20 (2H, m), 5.02 (1H, 6, J 3.3 Hz CHOCOCl).

Fuente