反应详情

温度

-78 °C

Under dry N2, diisopropylamine (1.7 ml, 0.012 mol) was dissolved in tetrahydrofuran (20 ml) and cooled to -78° C. Butyl lithium (6.88 ml of 1.6 M in hexane, 0.011 mol) was added, and the mixture stirred at -20° C for 0.5 hour and then recooled to -78° C. 6-Bromo-3,4-dihydro-1(2H)-naphthalenone (2.25 g, 0.010 mol; J. Am. Chem. Soc. v. 102, p. 7920, 1980), dissolved in tetrahydrofuran (10 ml) was added, the mixture warmed to -20° C. over 0.5 hour and stirred at that temperature for 15 minutes. Finally benzyl bromide (1.3 ml, 0.011 mol) was added, the mixture warmed over 1 hour to ambient temperature, and stirred at that temperature for 16 hours. The reaction was quenched with two volumes of 10% HCl and extracted with 150 ml ether. The organic layer was washed with 100 ml saturated brine, dried (MgSO4), stripped in vacuo, and the residue chromatographed on silica gel using 1:1 hexane:CH2Cl2 as eluant, monitoring by tlc (1:2 hexane:CH2CL2). Recovered was 380 mg of bis-benzylated product (Rf 0.58), 750 mg of title product (Rf 0.50) and 1.1 g of starting material (Rf 0.28), suitable for recycling.

1. customrecooled to -78° C
2. additionwas added
3. temperaturethe mixture warmed to -20° C. over 0.5 hour
4. stirringstirred at that temperature for 15 minutes
5. temperaturethe mixture warmed over 1 hour to ambient temperature
6. stirringstirred at that temperature for 16 hours
7. customThe reaction was quenched with two volumes of 10% HCl
8. extractionextracted with 150 ml ether
9. washThe organic layer was washed with 100 ml saturated brine
10. dry with materialdried (MgSO4)
11. customthe residue chromatographed on silica gel using 1:1 hexane
12. customRecovered