反応 #1241

反応方程式

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

溶媒

THF

THF

反応条件

後処理

1. 1
   抽出extracted with ethyl ether
2. 2
   その他the organic phase decanted
3. 3
   乾燥dried over magnesium sulfate
4. 4
   その他evaporated
5. 5
   その他The residue obtained
6. 6
   その他was triturated in heptane
7. 7
   ろ過filtered
8. 8
   その他dried
9. 9
   その他6.12 g (93%) of ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate of melting point 199°-200° C. were recovered

実験手順

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.

出典