Pyridine → 2-adamantyl Chloroformate

HRID 1080533

Reaktionsgleichung

Reaktionsgleichung von HRID 1080533
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[OH:11])[CH2:8]2.[Cl:12][C:13]([O:16]C(=O)OC(Cl)(Cl)Cl)(Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[O:11][C:13]([Cl:12])=[O:16])[CH2:8]2

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 641492-AdamantanolHCID 94429Triphosgene

Produkt 1

HCID 108785372-adamantyl Chloroformate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  1. customThe solvent was removed in vacuo at 30° C.
  2. stirringstirred for 10 minutes
  3. filtrationThe pyridinium hydrochloride precipitate was filtered off
  4. customthe solvent removed in vacuo at 30° C.
  5. customto give an oil which

Quellen und Nachweise

ORD-Eintrag
ord-3e707e1279a34bd2ac9ccdac66487d85
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05580896

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