반응 #165136

반응 방정식

5-chloro-2-furaldehyde

isopropyl magnesium chloride

ammonium chloride

4-iodobenzonitrile

→

title compound

수율 105.4%

4-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile

수율 105.4%

용매

ethyl acetate

water

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to −78° C.
2. 2
   온도the temperature was gradually raised to 0° C
3. 3
   workup.WAITFollowing 30 minutes
4. 4
   workup.STIRRINGof stirring at 0° C.
5. 5
   추출to extract the reaction mixture
6. 6
   세척The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride
7. 7
   기타the solvent was evaporated under a reduced pressure
8. 8
   workup.ADDITIONEthyl acetate was added to the residue, which
9. 9
   여과was then filtered with NH silica gel
10. 10
    농축The filtrate was concentrated under a reduced pressure

실험 절차

To a mixture of 4-iodobenzonitrile (3.0 g, 13 mmol) and tetrahydrofuran (40 mL) was added dropwise isopropyl magnesium chloride (1-2 M diethyl ether solution, 11 mL, 11-22 mmol) at −78° C., which was stirred for 1 hour at 0° C. The reaction mixture was cooled to −78° C., 5-chloro-2-furaldehyde (2.2 g, 17 mmol) was added at that temperature, and the temperature was gradually raised to 0° C. Following 30 minutes of stirring at 0° C., saturated aqueous ammonium chloride solution, water and ethyl acetate were added to extract the reaction mixture. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. Ethyl acetate was added to the residue, which was then filtered with NH silica gel. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.2 g) as a crude product. This compound was used in the subsequent reaction without further purification.

출처