反应详情

温度

-10 °C

t-Butyl lithium (21.4 mL of a 1.7M solution in pentane, 36.4 mmol) was added dropwise to a suspension of CuCN (1.63 g, 18.2 mmol) in 120 mL of THF at -78° C. The mixture was stirred for 30 min and allowed to warm to -10° C. A soultion of 8.01 g (2S)-3-(2,3-diphenylmethylenedioxyphenyl)-1,2-epoxypropane (24.2 mmol) of (from step 3 above) in 20 mL of THF was added dropwise. The reactions was stirred for 18 hr, then quenched by addition of 100 mL of 9:1 saturated NH4Cl: conc. NH4OH. The mixture was stirred vigorously for 30 min and partitioned between 50 mL of water and 150 mL of ether. The aqueous phase was extracted twice with 50 mL of ether, and the combined layers were washed with water and saturated NH4Cl and dried over MgSO4. The solvents were removed under vacuum to give an amber oil. The oil was purified by flash chromatography over silica gel, eluting with 20% ethyl acetate:hexane to afford 5.95 g (63% yield) of the title compound as a yellow oil. MS (DCI/NH3) M/Z: 389 (M+H)+, 406 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 0.95 (s, 9H), 1.45 (m, 2H), 2.73 (dd, 1H), 2.85 (dd, 1H), 4.08 (m, 1H), 6.65-6.8 (m, 3H), 7.37 (m, 6H), 7.57 (m, 4H).

1. stirringThe reactions was stirred for 18 hr
2. customquenched by addition of 100 mL of 9:1 saturated NH4Cl
3. stirringThe mixture was stirred vigorously for 30 min
4. custompartitioned between 50 mL of water and 150 mL of ether
5. extractionThe aqueous phase was extracted twice with 50 mL of ether
6. washthe combined layers were washed with water and saturated NH4Cl
7. dry with materialdried over MgSO4
8. customThe solvents were removed under vacuum
9. customto give an amber oil
10. customThe oil was purified by flash chromatography over silica gel
11. washeluting with 20% ethyl acetate