Pyridine → 2-adamantyl Chloroformate

HRID 326721

Reaktionsgleichung

Reaktionsgleichung von HRID 326721
[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](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[Cl:12][C:13]([O:11][CH:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:15]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 641492-AdamantanolHCID 94429Triphosgene

Produkt 1

HCID 108785372-adamantyl ChloroformateAusbeute 207,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-adamantanol (912 mg, 5.99 mmol) in methylene chloride (15 mL), at 0° C. under nitrogen, was added a solution of triphosgene (653 mg, 2.2 mmol) and pyridine (484 μL, 5.99 mmol) in methylene chloride. The reaction mixture was stirred at ambient temperature for 3 hours and then concentrated to dryness under reduced pressure. Ethyl acetate was added to the residue and the resultant mixture was filtered. The filtrate was concentrated in vacuo to give 980 mg of the title compound as a white powder. 1H NMR (CDCl3) δ1.5-2.2 (m, 14H), 5.02 (m, 1H).

Aufarbeitung

  1. concentrationconcentrated to dryness under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. filtrationthe resultant mixture was filtered
  4. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7542839594044763989280a129f3bb2e
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270302

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