Réaction #302916

Équation de réaction

compound 3

[(S)-6-Benzyloxymetoxy-1,1,5-trimetyl-hexyloxy]-tert-butyldimethylsilane

hydrogen

→

alcohol

Rendement 77.0%

(s)-6-(tert-Butyldimethylsilyloxy)-2,6-dimethyl-heptan-1-ol

Rendement 77.0%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   AutreRemoval of BOM-protecting group in compound 3
2. 2
   workup.ADDITIONwas added 3 times per day
3. 3
   FiltrationThen, the mixture was filtered
4. 4
   Autrethe solvent was evaporated under reduced pressure
5. 5
   AutreThe oily residue was chromatographed on silica gel

Mode opératoire

Removal of BOM-protecting group in compound 3. (s)-6-(tert-Butyldimethylsilyloxy)-2,6-dimethyl-heptan-1-ol (4). 1st procedure. To a solution of compound 3 (1.5 g, 3.8 mmol) in ethyl acetate (10 mL) was added Pd/C (10%, 100 mg) at room temperature. The reaction mixture was stirred for 6 days under a continuous stream of hydrogen (from balloon) and Pd/C (100 mg in portions) was added 3 times per day. Then, the mixture was filtered and the solvent was evaporated under reduced pressure. The oily residue was chromatographed on silica gel using hexane/AcOEt (9:1) as an eluent yielding an oily alcohol 4 (0.80 g, 77%).

Source