Tetrabutylammonium Fluoride → 4-Ethynyloxan-4-ol

HRID 2422489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2422489
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]

Komponenten

5

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 597748684-[2-(Trimethylsilyl)ethynyl]oxan-4-ol

Produkt 1

HCID 155504854-Ethynyloxan-4-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-9d6ba52f372140779a9b635a6da2a1cb
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960409B2

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