تفاعل #82434

معادلة التفاعل

n-Butyl lithium

diphenylmethylenedioxybenzene

hexane

(S)-(+)-epichlorohydrin

Boron trifluoride etherate

→

title compound

المردود 58.0%

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

المردود 58.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched by addition of 50 mL of saturated NaHCO3
2. 2
   درجة الحرارةthe mixture was warmed to ambient temperature
3. 3
   أخرىpartitioned between 100 mL of ether and 100 mL of water
4. 4
   استخلاصThe aqueous phase was extracted with ether (2×40 mL)
5. 5
   غسيلwashed with brine
6. 6
   تجفيفdried over MgSO4
7. 7
   تركيزconcentrated in vacuo
8. 8
   أخرىto give a brown oil, which
9. 9
   أخرىwas purified by flash chromatography over silica gel
10. 10
    غسيلeluting with 15% ethyl acetate in hexane
11. 11
    أخرىto afford

الإجراء التجريبي

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).

المصدر