Pyridine → HCID 58137266, Verbindung

HRID 1424568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424568
[OH:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.N1C=CC=CC=1.[Cl:22][C:23](Cl)([O:25]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[Cl:22][C:23]([O:1][CH:2]1[CH:9]2[CH2:10][C:5]3([C:12]([O:14][CH3:15])=[O:13])[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2)=[O:25]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 3741502Methyl 4-hydroxyadamantane-1-carboxylate

Produkt 1

HCID 58137266HCID 58137266, VerbindungAusbeute 272,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A stirred solution of methyl 4-hydroxyadamantane-1-carboxylate (1.01 g, 4.8 mmol) and pyridine (0.38 mL, 4.8 mmol) in CH2Cl2 (25 mL) was cooled in an ice bath and a solution of triphosgene (0.48 g, 1.6 mmol) in CH2Cl2 (10 mL) was added dropwise over 15 min. The mixture ice bath was allowed to melt and the mixture was stirred for 3 h. The mixture was evaporated to dryness and the residue was triturated with EtOAc (100 mL). The filtrate was concentrated to afford 1-methoxycarbonyl-4-adamantyl chloroformate (1.19 g, 91%) as an oil which solidified on standing.

Aufarbeitung

  1. customThe mixture was evaporated to dryness
  2. customthe residue was triturated with EtOAc (100 mL)
  3. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3e3b9d157d3f43a4871374f2f7e246df
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927715B2

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