3,4-dihydro-2H-pyran → 2-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran

HRID 1712432

Reaktionsgleichung

Reaktionsgleichung von HRID 1712432
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][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)=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Komponenten

6

Edukt 4

HCID 80803,4-dihydro-2H-pyranHCID 1234974-Methyl-3-nitrobenzyl alcoholHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 685034882-(4-Methyl-3-nitrobenzyloxy)tetrahydropyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The solution of 9.85 g of 4-methyl-3-nitrobenzyl alcohol in 200 ml of dichloromethane is admixed successively with 10.9 ml of 3,4-dihydro-2H-pyran and 1.12 g of p-toluenesulphonic acid monohydrate. The reaction mixture is stirred at room temperature over 18 hours. The solution is poured onto 1M sodium hydrogencarbonate solution (300 ml) and extracted with tert-butyl methyl ether (2×300 ml). The organic phase is washed with brine (300 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.49 (1:2 EtOAc-heptane); Rt=4.73.

Aufarbeitung

  1. extractionextracted with tert-butyl methyl ether (2×300 ml)
  2. washThe organic phase is washed with brine (300 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-6689eb5700c143e7b2d2ba876daf3a32
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790715B2

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