m-Chloroperbenzoic acid → 3-Ethynyl-pyridine 1-oxide

HRID 1039618

Reaktionsgleichung

Reaktionsgleichung von HRID 1039618
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].ClC1C=C(C=CC=1)C(OO)=[O:14].[OH-].[Ca+2].[OH-]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[N+:5]([O-:14])[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acid2×HCID 1860033-EthynylpyridineHCID 6093208Calcium Hydroxide

Produkt 1

HCID 569723343-Ethynyl-pyridine 1-oxide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-ethynylpyridine in methylene chloride (5 mL/mmol) at room temperature was added m-chloroperoxybenzoic acid (m-CPBA, 70% purity, 1.2 eq) and the resulting mixture was stirred for 2 hours. A further amount of m-CPBA was added (0.25 eq) and stirring was continued for 1 hour. Calcium hydroxide was added (2 eq) and after 15 minutes the mixture was filtered through celite and the filtrate was evaporated. The solid residue was stirred in ether for 3 hours and filtered to afford the 3-ethynylpyridine N-oxide compound as a white solid.

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 hour
  3. filtrationafter 15 minutes the mixture was filtered through celite
  4. customthe filtrate was evaporated
  5. stirringThe solid residue was stirred in ether for 3 hours
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-e916da81413741589cd3cd7f52c30595
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552193B2

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