Sodium hydride → Methyl 2-[(4-iodobenzyl)oxy]-2-methylpropionate

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (55% in liquid paraffin) (315 mg, 7.3 mmol) in THF (2 ml) was dropped a solution of methyl 2-hydroxyisobutyrate (0.84 g, 7.1 mmol) in THF (2 ml). The reaction mixture was stirred for 30 minutes at 60° C. Thereto was dropped a solution of 4-iodobenzyl bromide (2.0 g, 6.7 mmol) in THF (4 ml) at 60° C. The mixture was stirred for 5 hours at 60° C. Therein were added ethyl acetate and a saturated ammonium chloride solution. After stirring for 5 minutes the mixture was separated by a separating funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give the subject compound (1.93 g, 86%).

Provenance & Evidence