Chlorotrimethylsilane → HCID 18433505, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(tert-butoxycarbonylamino)-7-(triisopropylsilyloxy) naphthalene, as described above in Step A, (12.47 g, 30.0 mmol) and N,N,N′,N′-tetramethylethylenediamine (10.0 mL, 66.0 mmol) in THF (300 mL) at −78° C. was added sec-butyllithium (1.3 M in cyclohexane, 24.2 mL, 31.5 mmol) dropwise. The reaction mixture was stirred at −78° C. for 5 min, then trimethylsilyl chloride (4.2 mL, 33.0 mmol) was added dropwise and stirring was continued for 30 min. sec-Butyllithium (1.3 M in cyclohexane, 24.2 mL, 31.5 mmol) was added and the mixture was stirred dropwise was stirred at −78° C. for 5 hours, then quenched with saturated aqueous NH4Cl (400 mL) and extracted with CH2Cl2 (2×500 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of hexane—30% to 50% CH2Cl2 to yield the above-titled product.

Provenance & Evidence