Реакция #1241

Уравнение реакции

ethyl 2-[7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-naphthyl]-4-thiophenecarboxylate

tetrabutylammonium fluoride

water

→

ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl ether
2. 2
   Другоеthe organic phase decanted
3. 3
   Сушкаdried over magnesium sulfate
4. 4
   Другоеevaporated
5. 5
   ДругоеThe residue obtained
6. 6
   Другоеwas triturated in heptane
7. 7
   Фильтрацияfiltered
8. 8
   Другоеdried
9. 9
   Другое6.12 g (93%) of ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate of melting point 199°-200° C. were recovered

Методика

8.29 g (15.2 mmol) of ethyl 2-[7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-naphthyl]-4-thiophenecarboxylate and 60 ml of THF were introduced into a round-bottomed flask. A solution of 15.2 ml (16.6 mmol) of tetrabutylammonium fluoride in THF (1.1N) was added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction medium was poured into water, extracted with ethyl ether, the organic phase decanted, dried over magnesium sulfate and evaporated. The residue obtained was triturated in heptane, filtered and dried. 6.12 g (93%) of ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate of melting point 199°-200° C. were recovered.

Источник