Methyl iodide → 5-Methoxyadamantan-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. After stirring the reaction mixture for 30 min., iodomethane (1.38 mL, 22 mmol) was added. The reaction mixture was warmed to room temperature and stirred for 16 h until TLC revealed completion of the reaction. Excess NaH was quenched by adding saturated aq. NH4Cl solution to the ice cooled reaction mixture. 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 crude reaction mass which was purified by column chromatography to yield 5-methoxyadamantan-2-one (3.0 g) in 83% yield. m/z (M+1), 181; 1H NMR (CDCl3) 300 MHz δ 3.26 (s, 3H), 2.67-2.61 (m, 2H), 2.39-2.33 (m, 1H), 2.20-1.93 (m, 10H).

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

ORDレコード

ord-9d9dfdb63cbe4460be7c3461ada9ed20

出典データセット

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07985759B2