反应详情

To a suspension of NaH (60% dispersed in nujol, 1.92 g, 80 mmol) in THF (80 mL) cooled to ice bath temperature was added 4-hydroxyadamantanone (6.64 g, 40 mmol) dissolved in THF (80 mL) via a syringe over a period of 15 minutes. After stirring the reaction mixture for 30 min., nBu4NI (1.4 g, 4 mmol) was added followed by the addition of benzylbromide (5.26 mL). The reaction mixture was warmed to room temperature and stirred for 16 h until TLC revealed disappearance of hydroxyadamantanone. Excess NaH was quenched by adding sat. 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 a crude reaction mass which was purified by column chromatography to obtain 5-(benzyloxy)adamantan-2-one as a gummy liquid (7.93 g) in 77% yield. m/z (M+1), 257; 1H NMR (CDCl3) 300 MHz δ 7.60-7.20 (m, 5H), 4.51 (s, 2H), 2.72-2.63 (m, 2H), 2.40-2.36 (m, 1H), 2.35-1.92 (m, 10H).

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