Réaction #2639

Équation de réaction

lithium aluminum hydride

4-tert-butyldimethylsiloxy-2-cyclopentenone

NaOH

→

title compound

Rendement 64.4%

cis-4-tert-butyldimethylsilyloxy-2-cyclopentenol

Rendement 64.4%

Conditions de réaction

Traitement

1. 1
   Autrebelow -15° C
2. 2
   FiltrationThe reaction is filtered through diatomaceous earth
3. 3
   Séchagedried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under vacuum

Mode opératoire

A stirred solution of ZnCl2 (19 mL, 19 mmol, 1M in ether) is treated with 4-tert-butyldimethylsiloxy-2-cyclopentenone (2.0 g, 9.42 mmol) under an atmosphere of argon. The solution is cooled to -20° C. and treated dropwise with lithium aluminum hydride (9.0 mL, 9.0 mmol, 1M in ether) at such a rate as to keep the reaction temperature at or below -15° C. After stirring for about 2 hours at -20° C., approximately 5 mL of 1N NaOH was added. The reaction is filtered through diatomaceous earth, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound (1.3 g); cis/trans/1-2+1-4 addition 81/3/16.

Source