Réaction #50360

Équation de réaction

(2R,3S,4S,5R)-5-(Triethylsilyloxy)-2,3-epoxy-2,4-dimethyl-1-octanol

n-butyllithium

Rochelle's salt

samarium diiodide

→

31

(2S,3S,4S,5R)-5-(Triethylsilyloxy)-3-hydroxy-2,4-dimethyloctanal

Solvants

THF

H2O

Et2O

Conditions de réaction

Traitement

1. 1
   Autreat 0° C.
2. 2
   AutreThe layers were separated
3. 3
   Extractionextracted with ether (3×5 ml)
4. 4
   Lavagewashed with 5% NaHCO3 (2×1 ml), brine (1×1 ml)
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated

Mode opératoire

(2R,3S,4S,5R)-5-(Triethylsilyloxy)-2,3-epoxy-2,4-dimethyl-1-octanol (21.0 mg, 69.4 μmol) in 300 μl of THF at 0° C. was deprotonated with 1.05 eq of n-butyllithium. After 15 min, 0.1M samarium diiodide (764 μmol, 1.1 eq) was added and the reaction was allowed to warm to 25° C. over night. Then 1 ml of 1/2 saturated Rochelle's salt was added, stirred an additional 1 h, and poured onto 5 ml of Et2O and 1 ml of H2O. The layers were separated, extracted with ether (3×5 ml), washed with 5% NaHCO3 (2×1 ml), brine (1×1 ml), dried over MgSO4 and concentrated to give 31 crude.

Source