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

HRID 1145

반응식

HRID 1145 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd8eb0b6bec94543a29935506ffa1165
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723499

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