Methyl iodide → 2-Methylcycloheptanone

Temperature

0 °C

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).

1. temperaturewas cooled to −78° C
2. stirringthe resulting mixture was stirred for 30 min at −78° C.
3. customThe cooling bath was removed
4. customto reach ambient temperature
5. stirringstirred at RT for 15 hours
6. custombefore being quenched with aqueous saturated NH4Cl
7. extractionThe mixture was extracted with DCM
8. washThe organic layer was washed with 0.1 M aqueous HCl and aqueous saturated NaHCO3
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated
12. distillationThe residue was purified by short path distillation

ORD record

ord-b3bf1fbd9f2845f4a118fc649e3baab8

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08012974B2