4-Toluenesulfonyl chloride → 2H-Pyran, 2-(5-hexenyloxy)tetrahydro-

HRID 1494115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494115
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.CCOCC>[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6]

Komponenten

6

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 80803,4-dihydro-2H-pyranHCID 699635-Hexen-1-ol

Produkt 1

HCID 111830362H-Pyran, 2-(5-hexenyloxy)tetrahydro-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 8.5 g 5-hexen-1-ol in 100 mL tetrahydrofuran is added 14 mL dihydropyran followed by 0.5 g p-toluenesulfonyl chloride. The mixture is stirred at room temperature for 18 hours and then diluted with ether. The mixture is then washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated. The resulting oil is chromatographed over silica gel using hexane/ether (18:1) as eluent to give 6-(2-tetrahydropyranyloxy)-hex-1-ene; NMR (CDCl3): delta 5.85 (m,1H), 4.6 (brs,1H).

Aufarbeitung

  1. washThe mixture is then washed with saturated aqueous sodium bicarbonate
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting oil is chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-01e4048ab9df4e4b847f85ac340b47b8
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05025025

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