Ethyl Bromide → 5-Ethoxyadamantan-2-one

To a suspension of NaH (60% dispersed in nujol, 0.96 g, 24 mmol) in THF (40 mL) cooled to ice bath temperature was added hydroxyadamantanone (3.32 g, 20 mmol) dissolved in THF (40 mL) via a syringe over a period of 15 minutes. The reaction mixture was stirred for 30 min then n-Bu4NI (0.74 g, 2 mmol) and ethyl bromide (1.6 mL, 22 mmol) were added. The reaction mixture was warmed to room temperature and stirred for 16 h. After cooling the reaction mixture to 0° C., the excess NaH was quenched by adding sat. aq. NH4Cl solution. The two layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, and the solvent was evaporated under reduced pressure to obtain a crude reaction mass, which was purified by column chromatography to yield 5-ethoxyadamantan-2-one (3.0 g) in 77% yield. m/z (M+1) 195; 1H NMR (CDCl3) 300 MHz δ 3.47 (q, J=7.0 Hz, 2H), 2.67-2.60 (m, 2H), 2.38-2.30 (m, 1H), 2.13-1.78 (m, 10H), 1.17 (t, J=7.0 Hz, 3H).

1. temperaturecooled to ice bath temperature
2. stirringstirred for 16 h
3. temperatureAfter cooling the reaction mixture to 0° C.
4. customthe excess NaH was quenched
5. additionby adding sat. aq. NH4Cl solution
6. customThe two layers were separated
7. extractionthe aqueous layer was extracted with EtOAc
8. washThe combined organic layer was washed with brine
9. dry with materialdried over anhydrous Na2SO4
10. customthe solvent was evaporated under reduced pressure
11. customto obtain a crude
12. customreaction mass, which
13. customwas purified by column chromatography

ORD record

ord-f780310a403c4e6ba7a722f2142b4b3b

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985759B2