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Ethyl Acetate → 17,17-Bis-(ethylenedioxy)-13-(cis-2-chlorovinyl)-10-methyl-gon-5-ene

HRID 972268
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 972268
C([Li])CCC.[Cl-].[Cl:7][CH2:8][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:28]1[CH2:42][O:41][C:36]23[O:37][CH2:38][CH2:39][O:40][C:30]2([C@:31]2([CH2:55][CH2:54][C@H:53]4[C@@H:43]([CH2:44][CH:45]=[C:46]5[C@:51]4([CH3:52])[CH2:50][CH2:49][CH2:48][CH2:47]5)[C@@H:34]2[CH2:35]3)[CH:32]=O)[O:29]1.C(OCC)(=O)C>CCCCCC.O1CCCC1.N1CCCCC1>[CH2:39]1[CH2:38][O:37][C:55]23[O:41][CH2:42][CH2:28][O:29][C:30]4([C@:31]2(/[CH:32]=[CH:8]\[Cl:7])[C@H:34]([C@@H:43]2[CH2:44][CH:45]=[C:46]5[C@:51]([CH3:52])([CH2:50][CH2:49][CH2:48][CH2:47]5)[C@H:53]2[CH2:54]3)[CH2:35][CH2:36]4)[O:40]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 197823(Chloromethyl)triphenylphosphonium chlorideHCID 8673512317,17-Bis-(ethylenedioxy)-androst-5-en-18-alHCID 178418339Butyllithium

Produkt 1

HCID 8673512217,17-Bis-(ethylenedioxy)-13-(cis-2-chlorovinyl)-10-methyl-gon-5-ene

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel
HCID 8082PiperidineLösungsmittel

Versuchsvorschrift

8.4 ml of a 1.56 molar solution of butyl-lithium in hexane is added to a suspension of 5.82 g of chloromethyltriphenyl-phosphonium chloride in 107 ml of absolute tetrahydrofurane and 1.67 ml of piperidine at 0° C, under argon and with complete exclusion of moisture. After 30 minutes, 1.3 g of 3,3:17,17-bis-(ethylenedioxy)-androst-5-en-18-al in 22.5 ml of tetrahydrofurane are added dropwise at room temperature. Thereafter, the mixture is stirred for 1 hour at room temperature and then poured into ice water. Ethyl acetate is added to the mixture and the organic phase is separated off and washed with cold 1 N hydrochloric acid, with water, with sodium bicarbonate solution and with saturated sodium chloride solution. After drying over sodium sulphate and evaporating the solvent, the residue is chromatographed on silica gel using a mixture of hexane/ethyl acetate (9:1). 3,3;17,17-Bis-(ethylenedioxy)-13-(cis-2-chlorovinyl)-10-methyl-gon-5-ene is isolated from the first fractions and is recrystallised from methylene chloride/hexane; melting point 172°-174° C, [α]D 25 = -81°. The corresponding trans isomer is obtained from the later fractions and after recrystallisation from petroleum ether melts at 108°-110° C, and has an [α]D25 = -52°.

Aufarbeitung

  1. customthe organic phase is separated off
  2. washwashed with cold 1 N hydrochloric acid, with water, with sodium bicarbonate solution and with saturated sodium chloride solution
  3. dry with materialAfter drying over sodium sulphate
  4. customevaporating the solvent
  5. customthe residue is chromatographed on silica gel using
  6. additiona mixture of hexane/ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b84356c327424cc6a1f76f2cd23b5ea9
Quelldatensatz
uspto-grants-1977_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04052421

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