Reaktion #460079

Reaktionsgleichung

sodium borohydride

ethyl 8-acetyl-12-methyl-11-heptadecenoate

sodium hydroxide

sodium hydroxide

→

Ethyl 8-Acetyl-12-hydroxy-12-methylheptadecanoate

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto give
2. 2
   workup.ADDITIONa suspension of a yellow solid
3. 3
   workup.WAITAfter 6 hours
4. 4
   Sonstigea cloudy solution results
5. 5
   SonstigeLiquids are decanted from the precipitated mercury
6. 6
   Waschenwashed with three portions of water
7. 7
   Trocknendried over sodium sulfate
8. 8
   SonstigeEvaporation of the ether
9. 9
   Sonstigeleaves 4.4 g
10. 10
    Sonstigeof ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification

Vorschrift

Mercuric acetate (3.8 g., 0.012 mole) is dissolved in water (12 ml.) and tetrahydrofuran (20 ml.) is added to give a suspension of a yellow solid. Then, ethyl 8-acetyl-12-methyl-11-heptadecenoate (4.2 g., 0.012 mole) in tetrahydrofuran (20 ml.) is added, and the mixture stirred at room temperature for 24 hours. After 6 hours, the yellow suspended solid has disappeared and a cloudy solution results. To the solution is added 3M sodium hydroxide solution (12 ml.), followed by 0.5M sodium borohydride solution is 3M sodium hydroxide (12 ml.). Liquids are decanted from the precipitated mercury. The organic layer is taken up in ether, washed with three portions of water and dried over sodium sulfate. Evaporation of the ether leaves 4.4 g. of ethyl 8-acetyl-12-hydroxy-12-methylheptadecanoate as a yellowish oil used in the next step without further purification; pmr (CDCl3) δ 0.88 (3H,t), 1.13 (3H,s, CH3COH), 1.25 (3H,t, CH3CH2OCO--), 2.12 (3H,s, CH3CO), 4.12 (2H,q).

Quelle