Реакция #321443

Уравнение реакции

Sodium hydride

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

thiophenol

→

desired compound

Выход 83.3%

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

Выход 83.3%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   ТемператураAfter the reaction mixture was cooled
2. 2
   Экстракцияthe product was extracted with ethyl acetate
3. 3
   ПромывкаThe extract was washed with water
4. 4
   Другоеdried
5. 5
   workup.DISTILLATIONthe solvent was distilled off
6. 6
   ДругоеThe residue was purified by column chromatography on silica gel (isopropyl ether-ethyl acetate, 1:1)
7. 7
   Другоеthe purified product was recrystallized from ethanol-isopropyl ether

Методика

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.

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