Réaction #1502

ord-169f88b27a294c15b3d94e8de0e682c6

Équation de réaction

O=C(Cl)OCCl
Chloromethyl chloroformate
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesterol
c1ccncc1
Pyridine
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@](O)(C(=O)OCCl)CC[C@]4(C)[C@H]3CC[C@]12C
3-(Chloromethoxycarbonyl) Cholesterol

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureThe solution was cooled
  2. 2
    TempératureHeat
  3. 3
    Autrewas produced
  4. 4
    Autrethe reaction gave a clear solution from
  5. 5
    Lavagewashed with 0.5M HCl (50 ml) and water (3×25 ml)
  6. 6
    AutreAfter treatment with MgSO4, the solution was evaporated to dryness

Mode opératoire

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

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05725840uspto-grants-1998_03