Tetrahydrofuran → alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

HRID 840453노트

반응식

HRID 840453 반응식
C[Si](C)(C)[C:3]#[C:4][C:5]1[C:14]2[C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:10]([CH3:18])([CH3:17])[C:9]=2[CH:8]=CC=1CO.[CH2:23]1C[O:26][CH2:25][CH2:24]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:24]([CH:25]([C:3]1[CH:4]=[CH:5][C:14]2[C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][C:10]([CH3:17])([CH3:18])[C:9]=2[CH:8]=1)[OH:26])#[CH:23]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86752031alpha-Trimethylsilylethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

생성물 1

HCID 11817362alpha-Ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol

시약·촉매·용매 1

HCID 962Water용매

실험 절차

29.9 g (92.5 mmol) of α-trimethylsilylethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol and 100 ml of THF were introduced into a round-bottomed flask and 103.8 ml (114.2 mmol) of a tetrabutylammonium fluoride solution (1.1M in THF) were added dropwise. Stirring was carried out at room temperature for one hour and the reaction mixture was poured into water and extracted with ethyl ether. The organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a silica column eluted with a mixture of ethyl acetate and hexane (1/4). After evaporating the solvents, 18.1 g (79%) of α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol, with a melting point of 56°-57° C., were recovered.

후처리

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica column
  7. washeluted with a mixture of ethyl acetate and hexane (1/4)
  8. customAfter evaporating the solvents, 18.1 g (79%) of α-ethynyl-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenemethanol
  9. customwith a melting point of 56°-57° C., were recovered

출처 및 근거

ORD 기록
ord-0a9ccb01aa164da3a767c08ce812fe34
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06368608B1

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