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Sodium Sulfate → 17-Methylenestr-4-en-3beta-ol

HRID 1953492
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1953492
C(O[AlH-](OC(C)(C)C)OC(C)(C)C)(C)(C)C.[Li+].[CH2:18]=[C:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:34]([CH2:35][CH2:36][C@:20]12[CH3:21])[C@@H:33]1[C:28](=[CH:29][C:30](=[O:37])[CH2:31][CH2:32]1)[CH2:27][CH2:26]3.[O-]S([O-])(=O)=O.[Na+].[Na+]>CCOCC>[CH2:18]=[C:19]1[CH2:24][CH2:23][C@H:22]2[C@H:25]3[C@H:34]([CH2:35][CH2:36][C@:20]12[CH3:21])[C@@H:33]1[C:28](=[CH:29][C@@H:30]([OH:37])[CH2:31][CH2:32]1)[CH2:27][CH2:26]3
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24436Sodium SulfateHCID 1587099217-Methyleneestra-4-EN-3-oneHCID 16684435Lithium tritertbutoxyaluminohydride

Produkt 1

HCID 2287306917-Methylenestr-4-en-3beta-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Lithium tri-t-butoxyaluminohydride (766.6 mg, 3.015 mmol) was added to a solution of 17-methylenestr-4-en-3-one (16, 203.7 mg, 0.7533 mmol) in 10 ml of anh. ether and the reaction was stirred 420 h. See FIG. 161. Glauber's salt (3.80 g) was added and the suspension was stirred an additional 1/2 h. The mixture was filtered through diatomaceous earth and the residue was washed five times with 10 ml portions of ether. The combined filtrates were concentrated under reduced pressure and then subjected to preparative TLC (5% ethyl acetate/methylene chloride on silica gel GF, 1000 thickness) to give white needles (60.2 mg. 0.221 mmol, 29%) homogeneous to TLC (Rf 0.37, 5% ethyl acetate/methylene chloride on silica gel).

Aufarbeitung

  1. stirringthe suspension was stirred an additional 1/2 h
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. washthe residue was washed five times with 10 ml portions of ether
  4. concentrationThe combined filtrates were concentrated under reduced pressure
  5. customto give white needles (60.2 mg. 0.221 mmol, 29%) homogeneous to TLC (Rf 0.37, 5% ethyl acetate/methylene chloride on silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-23ec752ab0ba4e4cabb65d621abc256d
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06117860

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