Reaktion #1744644

Reaktionsgleichung

pyridinium bromide

4-(2,2-dimethyl-5-methoxy-7-n-pentylchroman-4-yl)-1-(2-naphthylmethyl) pyridinium bromide

sodium borohydride

→

2,2-Dimethyl-5-methoxy-4-[1-(2-naphthylmethyl)-1,2,5,6-tetrahydropyrid-4-yl]-7-n-pentylchroman

Lösungsmittel

ethanol

water

diethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added portionwise to the stirred solution at ambient temperature
2. 2
   workup.ADDITIONAt the end of the addition
3. 3
   SonstigeThe organic layer was separated
4. 4
   Trocknendried over anhydrous potassium carbonate
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   SonstigeThe residual amber gum (4.96g.) was purified via column chromatography on silica gel using 60°-80° petroleum ether/ethyl acetate mixtures as eluent

Vorschrift

This pyridinium bromide (5.86g.) was dissolved in a mixture of ethanol (70 ml.) and water (23 ml.) and sodium borohydride (0.74g.) was added portionwise to the stirred solution at ambient temperature. At the end of the addition, the solution was stirred for a further 0.5 hours and was then diluted with diethyl ether (300 ml.) and water (300 ml.). The organic layer was separated, dried over anhydrous potassium carbonate and evaporated under reduced pressure. The residual amber gum (4.96g.) was purified via column chromatography on silica gel using 60°-80° petroleum ether/ethyl acetate mixtures as eluent to give 2,2-Dimethyl-5-methoxy-4-[1-(2-naphthylmethyl)-1,2,5,6-tetrahydropyrid-4-yl]-7-n-pentylchroman as an orange oil (2.70g.).

Quelle