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

HRID 1577074

반응식

HRID 1577074 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-57b1180a1c3c4a3fb96826ff675ab9d0
출처 데이터셋
uspto-grants-1981_09
특허 번호
US04287129

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