반응 #321443

반응 방정식

Sodium hydride

2-bromomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran

thiophenol

→

desired compound

수율 83.3%

5-Formylamino-2,4,6,7-tetramethyl-2-phenylthiomethyl-2,3-dihydrobenzofuran

수율 83.3%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도After the reaction mixture was cooled
2. 2
   추출the product was extracted with ethyl acetate
3. 3
   세척The extract was washed with water
4. 4
   기타dried
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   기타The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1)
7. 7
   기타the purified product was recrystallized from ethanol-isopropyl ether

실험 절차

Sodium hydride (60% purity, 1.0 g, 21.1 mmol) was added to a solution of 2-bromomethyl-5-formylamino-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (6.0 g, 19.2 mmol) and thiophenol in dimethylformamide (50 ml) and the mixture was stirred at 80° C. for 1 hour under an argon atmosphere. After the reaction mixture was cooled, the product was extracted with ethyl acetate. The extract was washed with water, dried and the solvent was distilled off. The residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1) and then the purified product was recrystallized from ethanol-isopropyl ether to obtain the desired compound (5.54 g, yield: 83.3% yield), m.p. 130°-131° C.

출처