반응 #357280

반응 방정식

water

sodium hydride

1-benzyl-3-(5-chloro-2-fluorobenzyl)pyrrolidin-3-ol

dimethylformamide

→

subtitled compound

수율 46.0%

1′-Benzyl-5-chloro-3H-spiro[1-benzofuran-2,3′-pyrrolidine]

수율 46.0%

용매

toluene

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도the reaction mixture was refluxed for 90 minutes
3. 3
   추출extracted with ethyl acetate
4. 4
   건조The organic layer was dried over sodium sulphate (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타the residue was purified by silica gel flash chromatography (0-1.5% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH)

실험 절차

To a suspension of sodium hydride (NaH) (55%, 612 mg, 14.0 mmol) in toluene (10 mL) was added a solution of 1-benzyl-3-(5-chloro-2-fluorobenzyl)pyrrolidin-3-ol (1.3 g, 4.06 mmol) in toluene (20 mL) and the reaction mixture was kept on stirring at reflux, after 5 minutes dimethylformamide (10 mL) was added and the reaction mixture was refluxed for 90 minutes, cooled to room temperature, water (20 mL) was added and extracted with ethyl acetate. The organic layer was dried over sodium sulphate (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash chromatography (0-1.5% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH) to give the subtitled compound (560 mg).

출처