Iodoethane → HCID 68924621, compound

A solution of potassium tert-butoxide (1M in tBuOH) (160 mL, 160 mmol) was treated with cycloheptanone (5.4 mL, 45.8 mmol). The mixture stirred at room temperature for 5 minutes and was then put into an ice bath. Then, ethyl iodide (24 mL, 300 mmol) was added all at once. The reaction mixture stirred in the ice bath for 30 minutes and at room temperature overnight. After this time, the mixture was filtered, then the filtrate was evaporated to ˜15 mL. This crude mixture of mono and gem di-substituted products was combined with another 160 mL (160 mmol) of 1M potassium tert-butoxide, then after 5 minutes the mixture was put into an ice bath. Ethyl iodide (24 mL, 300 mmol) was added, and the reaction mixture was again stirred in the ice bath for 30 minutes and at room temperature overnight. The mixture was filtered after this time, and the filtrate was evaporated to ˜15 mL. This was partitioned between ether and water, and the ether layer was washed three times with water. The combined aqueous washes were then extracted three times with ether, then the combined organics were finally dried over Na2SO4 and evaporated. Chromatography on silica gel (3 to 20% EtOAc-hexane, eluant) afforded the title compound. 1H NMR (300 MHz, CDCl3) δ 2.50 (m, 2H), 1.86 (m, 1H), 1.57-1.69 (m, 6H), 1.33-1.49 (m, 4H), 1.23 (m, 1H), 0.75 (t, J=7.5 Hz, 6H).

1. customwas then put into an ice bath
2. filtrationAfter this time, the mixture was filtered
3. customthe filtrate was evaporated to ˜15 mL
4. additionThis crude mixture of mono and gem di-substituted products
5. waitafter 5 minutes the mixture was put into an ice bath
6. filtrationThe mixture was filtered after this time
7. customthe filtrate was evaporated to ˜15 mL
8. customThis was partitioned between ether and water
9. washthe ether layer was washed three times with water
10. extractionThe combined aqueous washes were then extracted three times with ether
11. dry with materialthe combined organics were finally dried over Na2SO4
12. customevaporated

ORD record

ord-24fb0f1f66de4a74a98bf49f2d6cf2ed

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436005B2