Ammonium Chloride → HCID 57049780, compound

Participants

Reaction Conditions

Reaction Steps

A 0.694 g (0.00346 mole) suspension of 20% potassium hydride in mineral oil is washed twice with petroleum ether and resuspended in 5 ml of tetrahydrofuran. The suspension is cooled with stirring at -15 ° C. and a solution of 1.169 g (0.00346 mole) of (2S,3S,4R)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-4-hydroxy-2-(3-pyridyl)tetrahydrofurane in 10 ml of tetrahydrofurane is added dropwise. After stirring the mixture for 2 min, 1.37 g (0.00346 mole) of 4-iodomethylbiphenyl is added at once and the mixture is stirred at -15° C. for 75 min. Concentrated ammonium chloride is added and the mixture is extracted with ether (2×20 ml). The combined extracts are washed with water and brine, dried (MgSO4) and evaporated. The residue is purified by flash chromatography using ethyl acetate-methylene chloride (1:1) to give (2S,3S,4R)-4-(biphenyl-4-ylmethoxy)-3-(3-t-butyldimethylsilyloxyprop-1-yl)-2 -(3-pyridyl)tetrahydrofuran as an oil having [α]D25 =+71.99 MeOH).

Provenance & Evidence