반응 #82435

반응 방정식

t-Butyl lithium

CuCN

(2S)-3-(2,3-diphenylmethylenedioxyphenyl)-1,2-epoxypropane

hexane

→

title compound

수율 63.0%

(2R)-4,4-Dimethyl-(2,3-diphenylmethylenedioxyphenyl)-2-pentanol

수율 63.0%

용매

pentane

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reactions was stirred for 18 hr
2. 2
   기타quenched by addition of 100 mL of 9:1 saturated NH4Cl
3. 3
   workup.STIRRINGThe mixture was stirred vigorously for 30 min
4. 4
   기타partitioned between 50 mL of water and 150 mL of ether
5. 5
   추출The aqueous phase was extracted twice with 50 mL of ether
6. 6
   세척the combined layers were washed with water and saturated NH4Cl
7. 7
   건조dried over MgSO4
8. 8
   기타The solvents were removed under vacuum
9. 9
   기타to give an amber oil
10. 10
    기타The oil was purified by flash chromatography over silica gel
11. 11
    세척eluting with 20% ethyl acetate

실험 절차

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).

출처