Реакция #321458

Уравнение реакции

2-Bromomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran

Sodium cyanide

→

desired compound

Выход 102.4%

2-Cyanomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran

Выход 102.4%

Растворители

water

Условия реакции

Обработка

1. 1
   Экстракцияthe product was extracted with ethyl acetate
2. 2
   ПромывкаThe extract was washed with water
3. 3
   Другоеdried
4. 4
   Концентрированиеconcentrated
5. 5
   ДругоеThe residue was purified by column chromatography on silica gel (hexaneisopropyl ether, 2:1)
6. 6
   ДругоеThe crude crystals obtained
7. 7
   Другоеwere recrystallized from methanol

Методика

2-Bromomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (6.5 g, 18.6 mmol) was dissolved in dimethylsufoxide (30 ml). Sodium cyanide (1.43 g, 88 mmol) was added and the resulting mixture was stirred at 80° C. for 18 hours. The reaction mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (hexaneisopropyl ether, 2:1). The crude crystals obtained were recrystallized from methanol to obtain the desired compound (4.1 g, yield: 79.7%), m.p. 58°-59° C.

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