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

HRID 546806노트

반응식

HRID 546806 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3cedfdb0aba641ec9ec0e5090a1a8383
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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