Tetrahydrofuran → Diethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl]silylbenzyl Alcohol

Participants

Reaction Steps

To a −78° C. solution of 2-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (1.34 g, 5.0 mmol) in 6.9 mL of THF was added n-butyllithium (1.6 M, 3.13 mL, 5.0 mmol). After ten minutes, the solution was added via cannula to a B78° C. solution of diethyldichlorosilane (0.61 mL, 5.0 mmol) and THF (4.4 mL) and stirring continued for 1 hour. In a second flask containing 4-bromobenzyl tert-butyldiphenylsilyl ether (Compound 1, 3.19 g, 7.5 mmol) and THF (2 mL) at −78° C. was added n-butyllithium (1.6 M, 4.69 mL, 7.5 mmol). After ten minutes, the contents of the second flask were added via canula to the first flask. After 30 minutes at −78° C., the reaction was quenched by the addition of 5 mL of saturated aqueous NH4Cl. The solution was poured into a separatory funnel containing water and hexane. The layers were separated and the aqueous layer was extracted 3 times with hexane. The combined organic layers were washed once with brine, and dried over magnesium sulfate, and the solvents were removed under reduced pressure. The residue was dissolved in 20 mL of THF and treated with 3.2 g of tetrabutylammonium flouride (Tbaf) adsorbed onto silica gel (1-1.6 mmol flouride per gram). The suspension was stirred for 5 hours at room temperature and then the silica gel was washed with ether, and the separated ether extracts were dried over magnesium sulfate. The filtered solvents were removed under reduced pressure and the residue purified by silica gel chromatography (9:1, hexane:ethyl acetate) to give the title compound.

Provenance & Evidence