3,4-dihydro-2H-pyran → HCID 22276215, Verbindung

HRID 1063936

Reaktionsgleichung

Reaktionsgleichung von HRID 1063936
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.[NH+]1C=CC=CC=1>ClCCl.C1(C)C(S([O-])(=O)=O)=CC=CC=1>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Komponenten

6

Edukt 3

HCID 80803,4-dihydro-2H-pyranHCID 899564-Chloro-2-nitrobenzyl alcoholHCID 4989215Pyridinium

Produkt 1

HCID 22276215HCID 22276215, VerbindungAusbeute 62,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3424274ToluenesulfonateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A magnetically stirred solution of 4-chloro-2-nitrobenzyl alcohol (25.0 g, 133 mmol) and 3,4-dihydro-2H-pyran (118.2 mL, 16.8 g, 200 mol) in anhydrous dichloromethane (250 mL) was treated at 25° C. with pyridinium (toluenesulfonate (PPTS, 50 mg). The solution was stirred for 12 h, washed with 1 N NaOH (250 mL), brine (250 mL), dried (K2CO3), filtered, and concentrated in vacuo. Silica gel chromatography (4:1 hexane:ethyl acetate) of the concentrate gave 22.5 g (62%) of the title compound as an oil.

Aufarbeitung

  1. washwashed with 1 N NaOH (250 mL), brine (250 mL)
  2. dry with materialdried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-476e4a958f394232a507765528dae39f
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967196B1

Verknüpfte Notizen

Wird geladen…