Sodium Bicarbonate → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-ol

HRID 918544

Reaktionsgleichung

Reaktionsgleichung von HRID 918544
C([O:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[OH:5][C@@H:6]1[C@:14]2([CH2:15][CH3:16])[C@H:9]([C@@H:10]3[CH2:24][CH2:23][C:22]4[CH:21]=[C:20]([O:25][CH3:26])[CH:19]=[CH:18][C:17]=4[C@H:11]3[CH2:12][CH2:13]2)[CH2:8][CH2:7]1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18595372(+)-17beta-Tert.butoxy-13 beta-ethyl-3-methoxygona-1,3,5(10)-triene

Produkt 1

HCID 66432(17beta)-13-Ethyl-3-methoxygona-1,3,5(10)-trien-17-olAusbeute 103,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 0.4 g (1.12 mmoles) of (+)-17β-tert.butoxy-13 β-ethyl-3-methoxygona-1,3,5(10)-triene and 0.1 g of p-toluenesulfonic acid monohydrate in 10 ml of toluene was stirred and heated at reflux for 1 hr. The resulting solution was cooled and treated with saturated aqueous sodium bicarbonate solution then extracted twice with ether. The combined organic extracts were dried, filtered and concentrated in vacuo giving 0.348 g of (+)-17β-hydroxy-13β-ethyl-3-methoxygona-1,3,5(10)-triene as a colorless solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1 hr
  3. temperatureThe resulting solution was cooled
  4. extractionthen extracted twice with ether
  5. customThe combined organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e68b4df0771a4eca8c89b8a157f3a9db
Quelldatensatz
uspto-grants-1976_07
Patentnummer
US03971809

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