Tetrahydrofuran → 4-Ethynyloxan-4-ol

HRID 657682Notes

Reaction equation

HRID 657682 reaction equation
[C:1]([Mg]Cl)#[CH:2].O1CCCC1.[O:10]1[CH2:15][CH2:14][C:13](=[O:16])[CH2:12][CH2:11]1.[Cl-].[NH4+]>C(OCC)C>[C:1]([C:13]1([OH:16])[CH2:14][CH2:15][O:10][CH2:11][CH2:12]1)#[CH:2]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 178462451HCID 178462451, compound

Product 1

HCID 155504854-Ethynyloxan-4-olYield 96.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethynylmagnesium chloride in tetrahydrofuran (0.5 M, 12 ML, 6.0 mmol) was added with cooling in ah ice-water bath to a solution of tetrahydro-4H-pyran-4-one (0.496 g, 5.0 mmol) in diethyl ether (300 mL) dropwise over 15 min. The mixture was stirred at room temperature for 1 h. Aqueous saturated ammonium chloride solution (1.0.0 mL) was then added and mixture extracted with ether (2×20 mL). The ether layers were washed with saturated aqueous sodium chloride solution (20 mL), then combined, dried over MgSO4, filtered and concentrated to give 4-ethynyl-tetrahydro-pyran-4-ol as a colorless oil that solidified on standing. (0.60 g, 96.2% yield).

Workup

  1. extractionmixture extracted with ether (2×20 mL)
  2. washThe ether layers were washed with saturated aqueous sodium chloride solution (20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4fdea07327ef48c38346b1e59964f9a0
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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