Tetrahydro-4H-pyran-4-one → 4-ethenyloxan-4-ol

HRID 2040227Notes

Reaction equation

HRID 2040227 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[CH:8]([Mg]Br)=[CH2:9]>C(OCC)C>[CH:8]([C:4]1([OH:7])[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)=[CH2:9]

Participants

4

Reactant 2

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 178418507HCID 178418507, compound

Product 1

HCID 3135164-ethenyloxan-4-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dihydro-2H-pyran-4(3H)-one (8.01 g) in anhydrous ethyl ether (50 mL) was treated with 1.0 M vinylmagnesium bromide (104 mL) over 20 minutes at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was quenched with saturated NH4Cl, and the organic layer was separated. The aqueous layer was extracted with additional ethyl ether three times. The combined organic layers were washed with brine, dried, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel using 20% ethyl acetate in hexanes to provide the title compound.

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with additional ethyl ether three times
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography on silica gel using 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d7f6a3635c7446ef9f9276d5e7686a8d
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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