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

HRID 1577074

反応式

HRID 1577074 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 2279738725-Hydroxycholesta-1,4,6-trien-3-one収率 149.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-57b1180a1c3c4a3fb96826ff675ab9d0
出典データセット
uspto-grants-1981_09
特許番号
US04287129

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