3,4-dihydro-2-methoxy-2H-pyran → 2H-Pyran-3-ol, tetrahydro-6-methoxy-

HRID 2299108Notes

Reaction equation

HRID 2299108 reaction equation
B.C1C[O:5]CC1.[CH3:7][O:8][CH:9]1[CH2:14][CH2:13][CH:12]=[CH:11][O:10]1>C1COCC1>[CH3:7][O:8][CH:9]1[O:10][CH2:11][CH:12]([OH:5])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 915383,4-dihydro-2-methoxy-2H-pyranHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 122006502H-Pyran-3-ol, tetrahydro-6-methoxy-Yield 217.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-THF 1M (14.6 ml, 14.6 mmol) was added slowly to an ice cooled solution of 3,4-dihydro-2-methoxy-2H-pyran (55.0 g, 44 mmol) in THF (15 ml). The ice bath was removed and the reaction was stirred at room temperature for 1 h, cooled to 0° C. and 3 N sodium hydroxide (14.6 ml) was added followed with 30% hydrogen peroxide (9 ml). This was allowed to stir for 4 hs warming to room temperature. The reaction was extracted with ethyl acetate (2×50 ml). The combined organic layer was washed with brine, dried over magnesium sulfate and concentrated to give 6-methoxytetrahydro-2H-pyran-3-ol (4.2 g, 72%) as an oil.

Workup

  1. customThe ice bath was removed
  2. temperaturecooled to 0° C.
  3. addition3 N sodium hydroxide (14.6 ml) was added
  4. stirringto stir for 4 hs
  5. temperaturewarming to room temperature
  6. extractionThe reaction was extracted with ethyl acetate (2×50 ml)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-48797f3fa4cc4de5b16be8d5d2d9d203
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Reaction notes

Loading…