4-Pentyn-1-ol → 2-(4-Pentynyloxy)tetrahydro-2H-pyran

HRID 1637100

Reaktionsgleichung

Reaktionsgleichung von HRID 1637100
[OH:1][CH2:2][CH2:3][CH2:4][C:5]#[CH:6].[OH2:7].[C:8]1(C)C=[CH:12][C:11](S(O)(=O)=O)=[CH:10][CH:9]=1>O1C=CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:12][CH2:11][CH2:10][C:9]#[CH:8]

Komponenten

4

Edukt 2

HCID 793464-Pentyn-1-olHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 3578162-(4-Pentynyloxy)tetrahydro-2H-pyranAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80803,4-dihydro-2H-pyranLösungsmittel

Versuchsvorschrift

A mixture of 5-hydroxypentyne (5.0 g, 0.06 mol) and freshly distilled dihydropyran (10 mL) was treated with a trace of p-toluenesulfonic acid hydrate. The exothermic reaction was stirred for 5 min, and the excess dihydropyran was removed under reduced pressure. The residue was purified by flash chromatography (alumna, neutral, activity 1, 25% ether/hexane) and gave the title compound (6.4 g, 63%). 1H NMR (400 MHz, CDCl3) δ 4.60 (t, 1 H), 3.86 (m, 2 H), 3.50 (m, 2 H), 2.32 (m, 2 H), 1.96 (t, 1 H), 1.82 (m, 3 H), 1.72 (m, 1 H), 1.48-1.65 (m, 4 H).

Aufarbeitung

  1. customThe exothermic reaction
  2. customthe excess dihydropyran was removed under reduced pressure
  3. customThe residue was purified by flash chromatography (alumna, neutral, activity 1, 25% ether/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-760c4bd2d9414d128b4dde8c4023a1ea
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06037367

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