Ethyl ketone → 1-(3-Benzyloxy-4-nitrophenyl)-2-methylpentan-3-one

Participants

Reaction Conditions

Reaction Steps

To a solution of pentan-3-one (516 mg, 6 mmol) in THF (5 mL) at −78° C. is added dropwise LiHMDS (6.6 mL of 1.0 M solution in THF, 6.6 mmol) over a period of 15 min. The solution is stirred at −78° C. for 2 h then a solution of 2-benzyloxy-4-bromomethyl-1-nitrobenzene (Example 83, step C) (963 mg, 3 mmol) in THF (5 mL) is added dropwise. The mixture is allowed to warm to RT overnight and is quenched with saturated ammonium chloride solution. The mixture is extracted with EtOAc and the organic phase is washed with brine then dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography using a gradient of 10-50% EtOAc/hexane as eluent to give the title compound.

Provenance & Evidence