3,4-dihydro-2H-pyran → 1-(tetrahydropyran-2-yloxy)-propan-2-one

HRID 2221133Notes

Reaction equation

HRID 2221133 reaction equation
[OH:1][CH2:2][C:3](=[O:5])[CH3:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:1][CH2:2][C:3](=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 8299HydroxyacetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 111163161-(tetrahydropyran-2-yloxy)-propan-2-oneYield 80.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-hydroxy-propan-2-one (95%, 78 g, 1.0 mol), 3,4-dihydro-2H-pyrane (95%, 88.5 g, 1.0 mol) and pyridinium p-toluenesulfonate (25.1 g, 0.1 mol) in THF (1.2 l) is stirred at room temperature for 16 hours. The mixture is diluted with ethyl acetate and repeatedly washed with brine. The organic phase is dried, filtered evaporated to afford 1-(tetrahydropyran-2-yloxy)-propan-2-one (127.8 g, 80.8%) as a liquid.

Workup

  1. washrepeatedly washed with brine
  2. customThe organic phase is dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-2c4970c2275e44cc96a5f5dce41d9a60
Source dataset
uspto-grants-2008_05
Patent number
US07368479B2

Reaction notes

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