반응 #82434

반응 방정식

n-Butyl lithium

diphenylmethylenedioxybenzene

hexane

(S)-(+)-epichlorohydrin

Boron trifluoride etherate

→

title compound

수율 58.0%

(2S )-3-chloro-1-(2,3-diphenylmethylenedioxyphenyl)-2-propanol

수율 58.0%

용매

THF

THF

반응 조건

후처리

1. 1
   기타The reaction was quenched by addition of 50 mL of saturated NaHCO3
2. 2
   온도the mixture was warmed to ambient temperature
3. 3
   기타partitioned between 100 mL of ether and 100 mL of water
4. 4
   추출The aqueous phase was extracted with ether (2×40 mL)
5. 5
   세척washed with brine
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated in vacuo
8. 8
   기타to give a brown oil, which
9. 9
   기타was purified by flash chromatography over silica gel
10. 10
    세척eluting with 15% ethyl acetate in hexane
11. 11
    기타to afford

실험 절차

n-Butyl lithium (2.3 mL of a 9.5M solution in hexane, 22 mmol) was added dropwise to a solution of 5.47 g of diphenylmethylenedioxybenzene (from step 1) in 75 mL of THF at 0° C. After 5 hr the solution was cooled to -78° C., and a solution of 1.85 g (20 mmol) of (S)-(+)-epichlorohydrin (Aldrich Chemical Co.) in 10 mL of THF was added. Boron trifluoride etherate (2.4 mL, 20 mmol) was then added dropwise, and the reaction was stirred for 1.5 hr. The reaction was quenched by addition of 50 mL of saturated NaHCO3, and the mixture was warmed to ambient temperature and partitioned between 100 mL of ether and 100 mL of water. The aqueous phase was extracted with ether (2×40 mL), and the ether extracts were combined and washed with brine, dried over MgSO4 and concentrated in vacuo to give a brown oil, which was purified by flash chromatography over silica gel, eluting with 15% ethyl acetate in hexane, to afford after removal of the solvent 4.23 g of the title compound as a light yellow oil (58% yield). MS (DCI/NH3) M/Z: 367 (M+H)+, 384 (M+NH4)+. 1H NMR (CDCl3, 300 MHz) δ: 2.3 (d, 1H), 2.9-3.0 (m, 2H), 3.5 (dd, 1H), 3.6 (dd, 1H), 4.1-4.23 (m, 1H), 6.65-6.85 (m, 3H), 7.37 (m, 6H), 7.55 (m, 4H).

출처