Reaktion #82434

Reaktionsgleichung

n-Butyl lithium

diphenylmethylenedioxybenzene

hexane

(S)-(+)-epichlorohydrin

Boron trifluoride etherate

→

title compound

Ausbeute 58.0%

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

Ausbeute 58.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by addition of 50 mL of saturated NaHCO3
2. 2
   Temperaturthe mixture was warmed to ambient temperature
3. 3
   Sonstigepartitioned between 100 mL of ether and 100 mL of water
4. 4
   ExtraktionThe aqueous phase was extracted with ether (2×40 mL)
5. 5
   Waschenwashed with brine
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto give a brown oil, which
9. 9
   Sonstigewas purified by flash chromatography over silica gel
10. 10
    Wascheneluting with 15% ethyl acetate in hexane
11. 11
    Sonstigeto afford

Vorschrift

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).

Quelle