Methyl iodide → 2-Methylcycloheptanone

Participants

Reaction Conditions

Reaction Steps

n-BuLi (2M solution) (35.86 mmol, 17.93 mL) was slowly added at 0° C. to a solution of DIPEA (5 mL, 35.86 mmol) in THF (45 mL). After stirred for 30 min at 0° C. the solution was cooled to −78° C. Cycloheptanone (4.0 gms, 4.2 mL, 35.66 mmol, 1.0 eqv) was added drop wise and the resulting mixture was stirred for 30 min at −78° C. before adding methyl iodide (2.96 mL, 47.4 mmol, 1.33 eq). The cooling bath was removed and the solution was allowed to reach ambient temperature and stirred at RT for 15 hours before being quenched with aqueous saturated NH4Cl. The mixture was extracted with DCM. The organic layer was washed with 0.1 M aqueous HCl and aqueous saturated NaHCO3, dried over Na2SO4, filtered, and evaporated. The residue was purified by short path distillation to give 2.8 g of 2-methyl-cycloheptanone (62% yield).

Provenance & Evidence