2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 25-Hydroxycholesta-1,4,6-trien-3-one

HRID 1577074

Reaktionsgleichung

Reaktionsgleichung von HRID 1577074
[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17]([CH2:18][C@H:19]([CH2:21][CH2:22]2)[OH:20])=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:4])[CH3:3].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[OH:1][C:2]([CH2:5][CH2:6][CH2:7][C@H:8]([C@@H:10]1[C@:28]2([CH3:29])[C@H:13]([C@H:14]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:17](=[CH:18][C:19](=[O:20])[CH:21]=[CH:22]2)[CH:16]=[CH:15]3)[CH2:12][CH2:11]1)[CH3:9])([CH3:3])[CH3:4]

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 6509425-Hydroxycholesterol

Produkt 1

HCID 2279738725-Hydroxycholesta-1,4,6-trien-3-oneAusbeute 149,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

25-Hydroxycholesterol (I) (10.0 gm, 0.0248 mol) was dissolved in 290 ml of dry dioxane. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (18.62 gm, 0.082 mol) was added and the reaction was refluxed 14 hours. The reaction mixture was allowed to cool and then filtered. The filtrate was concentrated, in vacuo, to give 14.7 gm red-brown solid. This solid was taken up in 40 ml ethyl acetate and chromatographed on 250 gm neutral alumina, eluting with ethyl acetate. Product-containing fractions were combined, concentrated and recrystallized from 50 ml ethyl acetate giving 5.80 g of the title compound (58%): m.p. 179.5°-181.5° C.; nmr (CDCl3): δ0.76 (s,3H,C19CH3), 1.20 (s,9H,C18 +C26 +C27CH3 's), 2.04 (s,1H,OH), 6.10 (m,4H,C2 +C4 +C6 +C7H's), 7.10 (d,J=12 Hz, 1H,C1H); UV (ethanol) λmax 225, 257, 299 nm.

Aufarbeitung

  1. temperaturethe reaction was refluxed 14 hours
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated, in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57b1180a1c3c4a3fb96826ff675ab9d0
Quelldatensatz
uspto-grants-1981_09
Patentnummer
US04287129

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