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

HRID 840453ノート

反応式

HRID 840453 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a9ccb01aa164da3a767c08ce812fe34
出典データセット
uspto-grants-2002_04
特許番号
US06368608B1

反応ノート

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