Tetrabutylammonium Fluoride → 1,1-dicyclopropylprop-2-yn-1-ol

HRID 2422492Notes

Reaction equation

HRID 2422492 reaction equation
[CH:1]1([C:4]([CH:12]2[CH2:14][CH2:13]2)([OH:11])[C:5]#[C:6][Si](C)(C)C)[CH2:3][CH2:2]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[CH:1]1([C:4]([CH:12]2[CH2:14][CH2:13]2)([OH:11])[C:5]#[CH:6])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59774911HCID 59774911, compound

Product 1

HCID 5201091,1-dicyclopropylprop-2-yn-1-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,1-dicyclopropyl-3-(trimethylsilyl)prop-2-yn-1-ol (2.25 g, 10.6 mmol) in THF (100 mL), a 1M solution of tetrabutyl ammonium fluoride in THF (37.2 mL, 37.2 mmol) was added. The reaction was then stirred 1 hour at room temperature. The reaction mixture was then poured into an aqueous 5% NH4OAc solution and diluted with ethyl acetate. The isolated organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography (ethyl acetate/hexanes, 20:80) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 4.17 (s, 1H), 2.75 (s, 1H), 1.25-1.15 (m, 2H), 0.65-0.55 (m, 2H), 0.55-0.30 (m, 6H).

Workup

  1. washThe isolated organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue obtained
  6. customwas purified by column chromatography (ethyl acetate/hexanes, 20:80)

Sources & evidence

ORD record
ord-e3a6c07d1e0d451db369585ddb20f501
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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