Reaktion #2458686

Reaktionsgleichung

citric acid

acetonitrile

(4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-4-hydroxytetrahydropyrane-2-one

lithium hydroxide

→

(3R,5S)-6-[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]-3,5-dihydroxyhexanoic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONan organic solvent was distilled away under reduced pressure at a temperature not more than 25° C
2. 2
   workup.DISSOLUTIONIn ether was dissolved the residue
3. 3
   Waschenthe mixture was washed with saturated brine solution
4. 4
   Sonstigedried
5. 5
   workup.DISTILLATIONdistilled away under reduced pressure

Vorschrift

To 1.6 ml of a solution of acetonitrile containing 150 mg (0.409 mmol) of (4R,6S)-6-[[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]methyl]-4-hydroxytetrahydropyrane-2-one was added 0.98 ml of 1N lithium hydroxide with stirring in an atmosphere of argon at -20° C. After 30 minutes thereto was added 3.9 ml of 0.1 M solution of citric acid, and an organic solvent was distilled away under reduced pressure at a temperature not more than 25° C. In ether was dissolved the residue and the mixture was washed with saturated brine solution, dried and distilled away under reduced pressure to give 157 mg of (3R,5S)-6-[(3,5-di-tert-butyl-4-hydroxyphenyl)thio]-3,5-dihydroxyhexanoic acid. Thereto was added 3.9 ml (0.389 mmol) of 0.1 N sodium hydroxide which was ice-cooled, washed with ether and freeze-dried to give 151 mg of the desired compound (yield: 89%).

Quelle