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

HRID 546806Notes

Reaction equation

HRID 546806 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-3cedfdb0aba641ec9ec0e5090a1a8383
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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