Tetrabutylammonium Fluoride → 4-Ethynyloxan-4-ol

HRID 2422489Notes

Reaction equation

HRID 2422489 reaction equation
C[Si]([C:5]#[C:6][C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)(=O)C>[C:6]([C:7]1([OH:13])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)#[CH:5]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 597748681044277-44-2

Product 1

HCID 155504854-Ethynyloxan-4-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-{(trimethylsilyl)ethynyl}tetrahydropyran-4-ol (1.0 g, 5.04 mmol) in THF (SnL), a 1 M solution of tetrabutyl ammonium fluoride in THF (5.29 mL, 5.29 mmol) was added and the reaction was stirred 2 hours 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 used as such for the next step. 1H NMR (400 MHz, acetone-d6): 4.61 (s, 1H), 3.87-3.77 (m, 2H), 3.60-3.50 (m, 2H), 2.98 (s, 1H), 1.89-1.81 (m, 2H), 1.77-1.65 (m, 2H).

Workup

  1. washThe isolated organic layer was washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9d6ba52f372140779a9b635a6da2a1cb
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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