Pyridine → 3-(Chloromethoxycarbonyl) Cholesterol

HRID 1406

Reaktionsgleichung

Reaktionsgleichung von HRID 1406
Cl[C:2]([O:4][CH2:5][Cl:6])=[O:3].[CH3:7][CH:8]([CH2:10][CH2:11][CH2:12][C@H:13]([C@@H:15]1[C@:33]2([CH3:34])[C@H:18]([C@H:19]3[C@H:30]([CH2:31][CH2:32]2)[C@:28]2([CH3:29])[C:22]([CH2:23][C@H:24]([CH2:26][CH2:27]2)[OH:25])=[CH:21][CH2:20]3)[CH2:17][CH2:16]1)[CH3:14])[CH3:9].N1C=CC=CC=1>C(Cl)Cl>[Cl:6][CH2:5][O:4][C:2]([C@:24]1([OH:25])[CH2:26][CH2:27][C@@:28]2([CH3:29])[C:22](=[CH:21][CH2:20][C@@H:19]3[C@@H:30]2[CH2:31][CH2:32][C@@:33]2([CH3:34])[C@H:18]3[CH2:17][CH2:16][C@@H:15]2[C@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH:8]([CH3:9])[CH3:7])[CH2:23]1)=[O:3]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 5997CholesterolHCID 62754Chloromethyl chloroformate

Produkt 1

HCID 571798753-(Chloromethoxycarbonyl) Cholesterol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureThe solution was cooled
  2. temperatureHeat
  3. customwas produced
  4. customthe reaction gave a clear solution from
  5. washwashed with 0.5M HCl (50 ml) and water (3×25 ml)
  6. customAfter treatment with MgSO4, the solution was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-169f88b27a294c15b3d94e8de0e682c6
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05725840

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