Methyl iodide → 6-Methylspiro[2.5]octan-5-one

Participants

Reaction Conditions

Reaction Steps

Spiro[2.5]octan-5-one (2.4 g, 19.32 mmol) was dissolved in THF (100 mL) and cooled to −75° C. At that temperature LHMDS 1M in THF (24 mL, 24 mmol) was added dropwise over 15 minutes. The resulting pale yellow solution was stirred 1 hour at −75° C. Iodomethane (1.3 mL, 21.26 mmol) was added and stirring was continued at −75° C. for another hour before letting the mixture warm up to RT. The reaction was quenched by addition of saturated aqueous NH4Cl. The layers were separated and the aqueous layer was extracted with Et2O. The combined organic layers were washed with brine, dried (Na2SO4), filtered and evaporated. The remaining yellow oil was purified by SiO2 chromatography (330 g SiO2, hexanes/EtOAc 0 to 3% EtOAc) to give 0.93 g of racemic 6-methyl-spiro[2.5]octan-5-one as a colorless liquid (35% yield).

Provenance & Evidence