Réaction #6156

Équation de réaction

(3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one

t-butyldimethylchlorosilane

ether

→

(3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one

Rendement 63.5%

Solvants

DMF

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixtures
2. 2
   Lavagewashed with 1N hydrochloric acid
3. 3
   AutreThe organic phase was dried
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated
6. 6
   AutreThe material obtained
7. 7
   Autrewas chromatographed on silica gel

Mode opératoire

M)d) 1.5 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-hydroxy-6-undecyl-2H-pyran-2-one were dissolved in 8 ml of DMF. 0.85 g of t-butyldimethylchlorosilane in 4 ml of DMF were then added dropwise. The mixture was stirred for 48 hours. The reaction mixtures was poured in to 100 ml of ether and washed with 1N hydrochloric acid. The organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was obtained 1.26 g of (3S,4S,6R)-tetrahydro-3-hexyl-4-[(t-butyldimethylsilyl)oxy]-6-undecyl-2H-pyran-2-one, MS: 411 (M+ -t-butyl).

Source