4-Toluenesulfonyl chloride → HCID 86746923, Verbindung

HRID 1587034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587034
[OH:1][C@@H:2]1[CH2:24][CH2:23][C@@:22]2([CH3:25])[C@H:4]([CH2:5][CH2:6][C:7]3[C@@H:21]2[CH2:20][C@H:19]([OH:26])[C@@:18]2([CH3:27])[C:8]=3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15][OH:16])[CH2:3]1.C(N(CC)CC)C.[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>C(Cl)Cl.C(#N)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C.CO>[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([O:16][CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:11]2[C@:18]3([CH3:27])[C:8](=[C:7]4[C@H:21]([CH2:20][C@@H:19]3[OH:26])[C@:22]3([CH3:25])[C@@H:4]([CH2:3][C@H:2]([OH:1])[CH2:24][CH2:23]3)[CH2:5][CH2:6]4)[CH2:9][CH2:10]2)[CH3:17])(=[O:43])=[O:42])=[CH:37][CH:36]=1

Komponenten

7

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 67857083HCID 67857083, Verbindung

Produkt 1

HCID 86746923HCID 86746923, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 21584119Ethylacetate methanolLösungsmittelHCID 21877088Acetonitrile methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 3α, 12α-dihydroxy-5β-chol-8(14)-en-24-ol (12.8 g) in methylene chloride/acetonitrile (1:1) (180 ml) is cooled to -5° C. Triethylamine (6 ml), 4-dimethylaminopyridine (0.435 g), and p-toluenesulfonyl chloride (6.65 g) are added and the solution stirred at 0° to 4° C. for about 18 hours. The solution is diluted with ethyl acetate/methanol (9:1), washed with brine and the organic solution dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product is purified by flash chromatography in ether, followed by 10% methanol in ethyl acetate to give the desired product.

Aufarbeitung

  1. washwashed with brine
  2. dry with materialthe organic solution dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified by flash chromatography in ether

Quellen und Nachweise

ORD-Eintrag
ord-c443b81df01f4e28b3a7a1b1f329a67d
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216015

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