2-Cyclohexen-1-one → HCID 15934054, compound

Temperature

-45 °C

To a suspension of anhydrous CuCN (2.16 g, 0.025 mol) in anhydrous ether (100 mL) at -78° C. was added tert butyllithium (29.0 mL of 1.7M solution in pentane, 0.05 mol). After being stirred at -78° C. for 1 hr and at -45° C. for 30 minutes, the reaction mixture was recooled to -78° C. A solution of cyclohexenone (2.4 g,0.025 mol) in ether (25 mL) was added and stirring continued for 15 minutes at -78° C. and at -45° C. for 30 minutes. The resulting mixture was recooled to -78° C., and HMPA (10 mL) in ether (25 mL) was added. After 5 min, methyl cyanoformate (2.55 g, 0.03 mol) in ether (25 mL) was added and the reaction warmed to 0° C. over a 2 hr period. The resulting mixture was quenched with 2N HCl (100 mL), the layers were separated, and the organic phase was washed with saturated NH4Cl solution (3×50 mL), water (2×50 mL), brine (1×50 mL) and dried (Na2SO4). Removal of the solvent in vacuo and purification by Kugelrohr distillation (bath temperature 100°-115° C. at 0.6 mm) afforded 4.7 g (88%) of methyl 2-(1,1-dimethylethyl)cyclohexan-6-one-carboxylate.

1. customwas recooled to -78° C
2. stirringstirring
3. waitcontinued for 15 minutes at -78° C. and at -45° C. for 30 minutes
4. customwas recooled to -78° C.
5. waitAfter 5 min
6. temperaturethe reaction warmed to 0° C. over a 2 hr period
7. customThe resulting mixture was quenched with 2N HCl (100 mL)
8. customthe layers were separated
9. washthe organic phase was washed with saturated NH4Cl solution (3×50 mL), water (2×50 mL), brine (1×50 mL)
10. dry with materialdried (Na2SO4)
11. customRemoval of the solvent
12. customin vacuo and purification
13. distillationby Kugelrohr distillation (bath temperature 100°-115° C. at 0.6 mm)

ORD record

ord-515006acacb04617b39f9ad2b15dfa3b

Source dataset

uspto-grants-1998_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05783589