反应详情

温度

95 °C

A slurry of 1.2 g. (50 mmoles) of sodium hydride (2.1 g. of 57% oil dispersion, washed with ether to remove the oil) in 25 ml. of dimethyl sulfoxide was stirred while 9.6 g. (50 mmoles) of 1-benzyl-3,4-dihydroxypyrrolidine, cis isomer, in 25 ml. of dimethyl sulfoxide was added. The mixture was stirred at ambient temperature for one hr., then 50 ml. of dimethyl sulfoxide was added and the temperature was raised to 95° C. for 0.5 hr. Mechanical stirring of the thick slurry was necessary while 13 g. (100 mmoles) of m-chlorofluorobenzene was added. During the heating period of 1 hr. at 95° C., all precipitate dissolved. The reaction mixture was concentrated by vacuum distillation of the dimethyl sulfoxide and excess m-chlorofluorobenzene. The residue was poured into water and extracted with hot cyclohexane. The organic extracts were combined, dried over anhydrous sodium sulfate and concentrated to give 7.5 g. (49%) of off-white crystals, m.p. 86°-87.5° C.

1. washof 57% oil dispersion, washed with ether
2. customto remove the oil) in 25 ml
3. stirringThe mixture was stirred at ambient temperature for one hr
4. stirringMechanical stirring of the thick slurry
5. customDuring the heating period of 1 hr
6. dissolutionat 95° C., all precipitate dissolved
7. concentrationThe reaction mixture was concentrated by vacuum distillation of the dimethyl sulfoxide and excess m-chlorofluorobenzene
8. additionThe residue was poured into water
9. extractionextracted with hot cyclohexane
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated
12. customto give 7.5 g