Cornforth reagent → 6-Methoxyoxan-3-one

HRID 2299109Notes

Reaction equation

HRID 2299109 reaction equation
C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O.[CH3:22][O:23][CH:24]1[O:29][CH2:28][CH:27]([OH:30])[CH2:26][CH2:25]1>C(Cl)Cl>[CH3:22][O:23][CH:24]1[O:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 122006502H-Pyran-3-ol, tetrahydro-6-methoxy-

Product 1

HCID 1282736-Methoxyoxan-3-oneYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

PDC (6.0 g, 28 mmol) was added to a solution of 6-methoxytetrahydro-2H-pyran-3-ol (2.0 g, 15 mmol) from step (394a) in methylene chloride (50 ml) at room temperature. The reaction was stirred overnight, filtered through silica gel and concentrated to give an oil. The product was distilled at 35° C. at 1000 mtorr pressure to give the 6-methoxydihydro-2H-pyran-3-(4H)-one (0.5 g, 25%) as an oil.

Workup

  1. filtrationfiltered through silica gel
  2. concentrationconcentrated
  3. customto give an oil
  4. distillationThe product was distilled at 35° C. at 1000 mtorr pressure

Sources & evidence

ORD record
ord-f135f214a31248988c78dccee744c0c9
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

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