Reaktion #1868683

Reaktionsgleichung

ethyl 5-cyano-4,4-diphenylpentanoate

lithium aluminum hydride

water

sodium hydroxide

water

→

title compound

Ausbeute 75.3%

5-Cyano-4,4-diphenylpentanol

Ausbeute 75.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.ADDITIONAfter completion of addition
3. 3
   workup.STIRRINGWhile the reaction mixture was stirred under ice-
4. 4
   Temperaturcooling
5. 5
   SonstigeThe insoluble matter that separated out
6. 6
   Filtrationwas filtered off
7. 7
   Extraktionthe filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate
8. 8
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
9. 9
   Trocknendried over anhydrous sodium sulfate
10. 10
    Einengenconcentrated to dryness
11. 11
    SonstigeThe group was purified by silica gel column chromatography

Vorschrift

To a stirred solution of ethyl 5-cyano-4,4-diphenylpentanoate (2 g) in tetrahydrofuran (25 ml) was added lithium aluminum hydride (0.37 g) in small portions under ice-cooling. After completion of addition, the mixture was further stirred for 30 minutes. While the reaction mixture was stirred under ice-cooling, water (0.9 ml), 15% aqueous sodium hydroxide (2.7 ml), and water (0.9 ml) were added in the order mentioned. The insoluble matter that separated out was filtered off and the filtrate was extracted with ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated to dryness. The group was purified by silica gel column chromatography to provide the title compound (1.3 g) as colorless syrup.

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