Réaction #1702066

Équation de réaction

5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene

pivaloyl chloride

→

5,6,7,8-tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl tert-butyl ketone

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Lavagethe organic layer was washed by water
2. 2
   Séchagea saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   AutreThe crude product was purified by silica gel chromatography

Mode opératoire

The synthesis process is as set forth in the chemical reaction formula below. The TiCl4 in the reaction path stands for titanium chloride. To 5,6,7,8-tetrahydro-2-hydroxy-5,5,8,8-tetramethylnaphthalene (409 mg, 2.00 mmol) were added titanium chloride (417 mg, 2.20 mmol) and pivaloyl chloride (361 mg, 2.99 mmol) followed by stirring at 120° C. for 1 hour. The reaction solution was diluted by dichloromethane, and the organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution, and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (40/3) as an elution solvent. The yield was 53.6 mg (9.0%).

Source