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Dichloromethane → 17,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

HRID 2059158
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2059158
[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[CH2:18][CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:46](Cl)Cl>COCOC>[C:1]([O:4][C@:5]1([C@:29]2([CH3:30])[C@H:15]([C@H:16]3[C@H:26]([CH2:27][CH2:28]2)[C@:24]2([CH3:25])[C:19](=[CH:20][C:21](=[O:31])[CH2:22][CH2:23]2)[C:18](=[CH2:46])[CH2:17]3)[CH2:14][CH2:13]1)[C:6](=[O:12])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 14812Phosphorus oxide (P4O10)2×HCID 10216517,21-Bis(acetyloxy)pregn-4-ene-3,20-dione

Produkt 1

HCID 1295177117,21-Diacetoxy-6-methylene-4-pregnene-3,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8020DimethoxymethaneLösungsmittel2×

Versuchsvorschrift

A solution of 5.0 g of 17,21-diacetoxy-4-pregnene-3,20-dione in 35 ml of anhydrous methylene chloride and 22.5 ml of methylal is combined in incremental portions at room temperature with a mixture of 1.0 g of phosphorus pentoxide and 7.5 g of silica gel. The mixture is agitated for 3 days at room temperature and then another 11 ml of methylal, 500 mg of phosphorus pentoxide, and 3.75 g of silica gel are added. After another 2 days, the reaction mixture is vacuum-filtered, the residue is washed thoroughly with methylene chloride, and evaporated to dryness under vacuum. The crude product is purified on 350 g of silica gel with a hexane/ethyl acetate gradient (0-50% ethyl acetate), thus obtaining 3.6 g of 17α,21-diacetoxy-6-methylene-4-pregnene-3,20-dione, mp 227°-228° C. [α]D25 =+165° (chloroform).

Aufarbeitung

  1. waitAfter another 2 days
  2. filtrationthe reaction mixture is vacuum-filtered
  3. washthe residue is washed thoroughly with methylene chloride
  4. customevaporated to dryness under vacuum
  5. customThe crude product is purified on 350 g of silica gel with a hexane/ethyl acetate gradient (0-50% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-4f9d0d0d87674fb89a42961937347e3b
Quelldatensatz
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04322349

Notizen zur Reaktion

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