Methanol → 7-Hydroxy-3-methoxybicyclo[4,3,0]non-3-ene

HRID 462780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462780
[H-].C([Al+]CC(C)C)C(C)C.[CH3:11][O:12][C:13]1[CH2:14][CH:15]2[CH:19]([CH2:20][CH:21]=1)[C:18](=[O:22])[CH2:17][CH2:16]2.CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[OH:22][CH:18]1[CH2:17][CH2:16][CH:15]2[CH:19]1[CH2:20][CH:21]=[C:13]([O:12][CH3:11])[CH2:14]2

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24436Sodium SulfateHCID 132409973-Methoxybicyclo[4,3,0]non-3-en-7-oneHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 132409987-Hydroxy-3-methoxybicyclo[4,3,0]non-3-eneAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

Diisobutylaluminium hydride (28.5 ml) was added dropwise to a stirred solution of 3-methoxybicyclo[4,3,0]non-3-en-7-one (20 g; prepared as described in Reference Example 1) in diethyl ether (600 ml), with cooling to -10° C. The resulting solution was stirred at 0° C. for 3 hours and then it was treated with methanol (20 ml). A gelatinous precipitate was formed, and the mixture was then treated with anhydrous sodium sulphate (200 g) and filtered with the aid of diatomaceous earth. The filtrate was concentrated at reduced pressure, to give 7-hydroxy-3-methoxybicyclo[4,3,0]non-3-ene (16 g).

Aufarbeitung

  1. customA gelatinous precipitate was formed
  2. filtrationfiltered with the aid of diatomaceous earth
  3. concentrationThe filtrate was concentrated at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8aa9fcbff6394c6687bf469fa036fba3
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04517202

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