Methanol → 21-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1973717
[C:1](OCC)(=[O:5])[CH2:2][CH2:3][CH3:4].[OH:9][C@@H:10]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[C:25](=[O:31])[CH2:24][C@@:23]2([CH3:32])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1.[H-].[Na+].CO>CS(C)=O>[C:1]([CH2:21][C:20](=[O:22])[C@@H:19]1[C@:23]2([CH3:32])[C@H:16]([C@H:15]3[C@H:26]([C:25](=[O:31])[CH2:24]2)[C@:27]2([CH3:30])[C@H:12]([CH2:11][C@H:10]([OH:9])[CH2:29][CH2:28]2)[CH2:13][CH2:14]3)[CH2:17][CH2:18]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 7762Ethyl butyrateHCID 24758Sodium hydrideHCID 104845Alphaxalone

Produkt 1

HCID 8673428421-Butyryl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Ethyl butyrate (0.84 ml) was added to a mixture of 3α-hydroxy-5α-pregnane-11,20-dione (665 mg) and sodium hydride (150 mg.) in dry dimethyl sulphoxide (10 ml.). The mixture was stirred, under N2, for 13/4 hrs. The reaction mixture was treated with methyl alcohol to destroy excess sodium hydride, then poured into 2N-hydrochloric acid. The product was extracted with ethyl acetate and the combined extracts were washed with water, dried and evaporated. Preparative t.l.c. of the residue (859 mg.) gave two fractions. The more polar fraction was title compound (244 mg.) [α]D + 74.0°, λmax. 278 nm (ε 12,980).

Aufarbeitung

  1. customto destroy excess sodium hydride
  2. additionpoured into 2N-hydrochloric acid
  3. extractionThe product was extracted with ethyl acetate
  4. washthe combined extracts were washed with water
  5. customdried
  6. customevaporated
  7. customof the residue (859 mg.) gave two fractions

Quellen und Nachweise

ORD-Eintrag
ord-04599ae8fc9c42da9ae36406e75c1e56
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US03998829

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