Reaction #1502

Reaction equation

Chloromethyl chloroformate

cholesterol

Pyridine

→

3-(Chloromethoxycarbonyl) Cholesterol

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   TemperatureThe solution was cooled
2. 2
   TemperatureHeat
3. 3
   Otherwas produced
4. 4
   Otherthe reaction gave a clear solution from
5. 5
   Washwashed with 0.5M HCl (50 ml) and water (3×25 ml)
6. 6
   OtherAfter treatment with MgSO4, the solution was evaporated to dryness

Procedure

Chloromethyl chloroformate (1.96 g, 15.2 mmol) and cholesterol (5.0 g, 12.9 mmol) was dissolved in CH2Cl2 (10 ml). The solution was cooled. Pyridine (1.21 g, 15.3 mmol) was dripped into the stirred solution over 5 minutes. Heat was produced and the reaction gave a clear solution from a somewhat unclear starting solution. After 24 hours at room temperature, the mixture was diluted with CH2Cl2 (50 ml), washed with 0.5M HCl (50 ml) and water (3×25 ml). After treatment with MgSO4, the solution was evaporated to dryness.

Source