Bicarbonate Ion → 7alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

HRID 361662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 361662
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)(O)[O-].C(Cl)(Cl)(Cl)[Cl:51]>C(#N)C.ClCCl>[Cl:51][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C@@H:7]1[CH2:24][C:23]2[C@H:18]([CH2:19][CH2:20][C:21](=[O:25])[CH:22]=2)[C@@H:17]2[C@@H:8]1[C@H:9]1[C@@:13]([CH2:15][CH2:16]2)([CH3:14])[C:12](=[O:26])[CH2:11][CH2:10]1

Komponenten

7

Edukt 4

HCID 769Bicarbonate IonHCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 158381567a-(5-Hydroxypentyl)-estr-4-ene-3,17-dione

Produkt 1

HCID 571565697alpha-(5-Chloropentyl)-estr-4-ene-3,17-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The same product is obtained from 8.05 g of 7α-(5-hydroxypentyl)-estr-4-ene-3,17-dione (Example 1b) by a 3.5-hour reaction with 8.66 g of triphenylphosphine in 85 ml of carbon tetrachloride and 30 ml of acetonitrile at room temperature. The reaction mixture is diluted with dichloromethane, shaken out with saturated bicarbonate solution and with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation in a vacuum. The residue is chromatographed on silica gel with dichloromethane and ethyl acetate, whereby 4.08 g of 7α-(5-chloropentyl)-estr-4-ene-3,17-dione is obtained, [α]D22 =+68°(c=0.5% in chloroform)

Aufarbeitung

  1. dry with materialdried with sodium sulfate
  2. concentrationconcentrated by evaporation in a vacuum
  3. customThe residue is chromatographed on silica gel with dichloromethane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8997c68cba6e4c99863c1eff4e5a70ec
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866560

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