Tetrahydrofuran → 4-Ethynyloxan-4-ol

HRID 366708

Reaction equation

HRID 366708 reaction equation
C([Mg]Cl)#C.[CH2:5]1[CH2:9][O:8][CH2:7][CH2:6]1.[O:10]1CC[C:13](=O)[CH2:12][CH2:11]1.[Cl-].[NH4+]>C(OCC)C>[C:12]([C:11]1([OH:10])[CH2:6][CH2:7][O:8][CH2:9][CH2:5]1)#[CH:13]

Participants

6

Reactant 4

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

Product 1

HCID 155504854-Ethynyloxan-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethynylmagnesium chloride in THF (0.5 M, 120 mL, 60 mmol) was added with cooling in an ice-water bath to a solution of tetrahydro-4H-pyran-4-one (4.96 g, 50 mmol) (Aldrich) in diethyl ether (300 mL) dropwise over 15 min. The mixture was stirred with cooling for 3 h. Aqueous ammonium chloride solution (100 mL, 15% W/V) was then added and mixture extracted with ether (2×200 mL). The ether layers were washed with saturated aqueous sodium chloride solution (200 mL), then combined, dried (MgSO4), filtered and concentrated to give 4-Ethynyl-tetrahydro-pyran-4-ol as a colorless oil that solidified on standing. (Yield 6.01 g, 96.2%).

Workup

  1. temperaturewith cooling for 3 h
  2. extractionmixture extracted with ether (2×200 mL)
  3. washThe ether layers were washed with saturated aqueous sodium chloride solution (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-07805d1f43314917b75bdcff125bf329
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Linked notes

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