Tetrabutylammonium Fluoride → 4-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol

HRID 546806ノート

反応式

HRID 546806 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:21]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([CH3:44])[CH:38]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[C:31][Si](C)(C)C)=[C:26]([CH3:36])[CH:25]=1)[CH2:22][CH3:23])[CH3:20]>O1CCCC1>[CH2:19]([C:21]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([CH3:44])[CH:38]=1)([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[CH:31])=[C:26]([CH3:36])[CH:25]=1)[CH2:22][CH3:23])[CH3:20]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 585983194-[1-Ethyl-1-(3-methyl-4-trimethylsilanylethynyl-phenyl)-propyl]-2-methyl-phenol

生成物 1

HCID 585982954-[1-Ethyl-1-(4-ethynyl-3-methyl-phenyl)-propyl]-2-methyl-phenol収率 102.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (78.3 mL, 78.3 mmol) was added to a solution of 4-[1-ethyl-1-(3-methyl-4-trimethylsilanylethynyl-phenyl)-propyl]-2-methyl-phenol (Example 1-(2); 19.03 g, 52.19 mmol) in tetrahydrofuran (520 mL) at room temperature. The mixture was stirred at 0.5 hour and concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by a silica gel column (hexane/ethyl acetate=10/1) to give the title compound (15.6 g, 94%).

後処理

  1. concentrationconcentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column (hexane/ethyl acetate=10/1)

出典と根拠

ORDレコード
ord-3cedfdb0aba641ec9ec0e5090a1a8383
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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