Pivalic anhydride → HCID 13423612, Verbindung

HRID 746156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 746156
O[C@@H:2]1[C@H:7]2[C@H:8]3[C:17]([CH2:18][CH2:19][C@:5]2([CH3:6])[C:4](=[O:21])[CH2:3]1)=[C:16]1[C:11](=[CH:12][C:13](=[O:20])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.C(OC(=O)C(C)(C)C)(=O)C(C)(C)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:6][C@:5]12[CH2:19][CH2:18][C:17]3[C@@H:8]([CH2:9][CH2:10][C:11]4[C:16]=3[CH2:15][CH2:14][C:13](=[O:20])[CH:12]=4)[C@@H:7]1[CH:2]=[CH:3][C:4]2=[O:21]

Komponenten

6

Edukt 3

HCID 15234Pivalic anhydrideHCID 516892Sodium BicarbonateHCID 1342360815alpha-Hydroxy-4,9-estradiene-3,17-dione

Produkt 1

HCID 13423612HCID 13423612, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A suspension of 19.5 g of 15α-hydroxy-4,9-estradiene-3,17-dione in 300 ml of toluene is mixed, under ice water cooling, successively with 26.5 g of pivalic acid anhydride and 18.6 g of 4-dimethylaminopyridine. Stirring is then performed for 72 hours at room temperature, then the reaction solution is poured into saturated sodium hydrogen carbonate solution, stirred for 30 more minutes at room temperature and extracted with ethyl acetate. The ethyl acetate extracts are washed with saturated ammonium chloride solution and saturated sodium chloride solution, dried with sodium sulfate and concentrated in a water jet vacuum. The crude product, thus obtained, is filtered with aluminum oxide, Merck, neutral, step III, with hexane/ethyl acetate. The main fraction is crystallized from ethyl acetate. 14.4 g (79% of theory) of 4,9,15-estratriene-3,17-dione with a melting point of 182° to 183° C. are obtained.

Aufarbeitung

  1. stirringstirred for 30 more minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate extracts are washed with saturated ammonium chloride solution and saturated sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in a water jet vacuum
  6. customThe crude product, thus obtained
  7. filtrationis filtered with aluminum oxide, Merck
  8. customThe main fraction is crystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-47f6b0d8c54840228178dcea94124f2a
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04603013

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