Diethyl Ether → ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate

Beteiligte Stoffe

Reaktionsschritte

To a mixture of (1S,2R,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (3) (4.66 g, 19.4 mmol)) and Et3N (7.01 mL, 50.4 mmol)) in DMF (40 mL) was added methanesulfonyl chloride (2.66 g, 23.3 mmol) dropwise at 0° C. After stirring at room temperature for 3 h, ether (400 mL) was added. The organics were washed with 1N HCl (20 mL), saturated aqueous sodium bicarbonate (20 mL), brine (2×20 mL), dried (Na2SO4), and concentrated to give ((1S,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)methyl methanesulfonate (12) (5.90 g, 96%) as a light yellow sticky mass.

Herkunft & Nachweise