1,4-Butanediol → 4-(Dimethyl-tert-butylsilyl)oxybutan-1-ol

Participants

Reaction Steps

To a solution of sodium hydride (1.3 g, 55.48 mmol) in anhydrous tetrahydrofuran (150 mL) at 0° C. under argon, was added a solution of 1,4-butanediol (5 g, 55.48 mmol) in anhydrous tetrahydrofuran (50 mL). The resulting mixture was stirred at room temperature for 45 minutes over which time a large amount of a white precipitate formed. t-Butyldimethylsilyl chloride (8.3 g, 55.48 mmol) was then added and the resulting mixture was stirred vigorously for 45 minutes and then diluted with diethyl ether (200 mL) and filtered. The filtrate was washed with 10% aqueous potassium carbonate (25 mL) and brine (2×50 mL). Purification by silica gel chromatography using hexane/ethyl acetate as eluent (7:3) gave 1-t-butyldimethylsilyloxy-4-hydroxybutane as a colorless oil (9.2 g, 80%). 1-t-Butyldimethylsilyloxy-4-hydroxybutane (2.0 g, 9.85 mmol), triphenylphosphine (3.07 g, 11.74 mmol) and diethyl azodicarboxylate (1.8 mL, 11.74 mmol) were added successively to a solution of 1,8-naphthalimide (1.92 g, 9.785 mmol) in anhydrous tetrahydrofuran (50 mL) at 0° C. under an atmosphere of argon. The reaction was allowed to warm to room temperature and stirred overnight. After removing the solvent under reduced pressure, the product was purified by silica gel chromatography using hexane/ethyl acetate (9:1) as the eluent to provide 4-t-butyldimethylsilyloxybutyl-1,8 naphthalimide as a colorless oil (3.68 g, 87%).

Provenance & Evidence