Water → Ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate

HRID 1145

Reaktionsgleichung

Reaktionsgleichung von HRID 1145
[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:25]=5)=[CH:18]4)=[CH:13][C:12]=3[O:31][Si](C(C)(C)C)(C)C)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[C:1]12([C:11]3[CH:20]=[C:19]4[C:14]([CH:15]=[CH:16][C:17]([C:21]5[S:22][CH:23]=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:25]=5)=[CH:18]4)=[CH:13][C:12]=3[OH:31])[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 19694679Ethyl 2-[7-(1-adamantyl)-6-tert-butyldimethylsilyloxy-2-naphthyl]-4-thiophenecarboxylate

Produkt 1

HCID 19694671Ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. extractionextracted with ethyl ether
  2. customthe organic phase decanted
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas triturated in heptane
  7. filtrationfiltered
  8. customdried
  9. custom6.12 g (93%) of ethyl 2-[7-(1-adamantyl)-6-hydroxy-2-naphthyl]-4-thiophenecarboxylate of melting point 199°-200° C. were recovered

Quellen und Nachweise

ORD-Eintrag
ord-dd8eb0b6bec94543a29935506ffa1165
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05723499

Verknüpfte Notizen

Wird geladen…