Acetic Acid → HCID 86741443, Verbindung

HRID 543023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543023
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]=[C:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])CP(=O)([O-])[O-].[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3CCC=O)(=[O:26])[CH3:25].C(O)(=O)C>CCCCCC.O1CCCC1>[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3[CH2:4][CH2:3][CH:2]=[CH:1][C:7](=[O:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:26])[CH3:25]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 20206901HCID 20206901, VerbindungHCID 86741444HCID 86741444, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 86741443HCID 86741443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

n-Butyl-lithium (0.341 ml. of a 1.6 molar solution in hexane) was added to a stirred solution of 2-oxotridecylphosphonate (0.193 g.) in tetrahydrofuran (10 ml.) which was maintained at -70° C. and the mixture was stirred at that temperature for 40 minutes. A solution of 3-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)propionaldehyde (Example 3; 0.2 g.) in tetrahydrofuran (10 ml.) was added and the mixture was allowed to warm up to laboratory temperature and was stirred at that temperature for 4.5 hours. Acetic acid was added until the mixture was acidic and the mixture was evaporated to dryness. Water (10 ml.) was added and the mixture was extracted three times with ethyl acetate (30 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and there was thus obtained as residual oil 1-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)hexadec-3-en-5-one.

Aufarbeitung

  1. temperatureto warm up to laboratory temperature
  2. stirringwas stirred at that temperature for 4.5 hours
  3. customthe mixture was evaporated to dryness
  4. additionWater (10 ml.) was added
  5. extractionthe mixture was extracted three times with ethyl acetate (30 ml
  6. washThe combined extracts were washed with water
  7. customdried
  8. customevaporated to dryness and there

Quellen und Nachweise

ORD-Eintrag
ord-580000efe708484dae508ec6c63cbafd
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04659516

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