Water → 5,5-dimethyltetrahydro-2H-pyran-2-one

HRID 217232Notes

Reaction equation

HRID 217232 reaction equation
O[CH2:2][C:3]([CH3:10])([CH3:9])[CH2:4][CH2:5][C:6]([OH:8])=[O:7].C([O-])([O-])=O.[K+].[K+].IC.O>CN(C=O)C>[CH3:2][C:3]1([CH3:10])[CH2:9][O:7][C:6](=[O:8])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 542561495-Hydroxy-4,4-dimethylpentanoic acid

Product 1

HCID 124481785,5-dimethyltetrahydro-2H-pyran-2-oneYield 57.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-hydroxy-4,4-dimethyl-pentanoic acid (300 mg, 2.05 mmol) in DMF (5 ml), K2CO3 (369 mg, 2.87 mmol) and iodomethane (154 ul, 2.47 mmol) are added at room temperature. The mixture is stirred at room temperature for 15 hours. To the mixture, H2O is added and the solution is extracted with AcOEt. The organic layer is washed with H2O, and brine, and dried over MgSO4, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography to give 5,5-dimethyl-tetrahydro-pyran-2-one (150 mg, 47%); TLC (hexane/AcOEt, 2:1) Rf 0.40, 1H NMR (400 MHz, chloroform-d) δ ppm 1.06 (s, 6H), 1.70 (t, 2H), 2.56 (t, 2H), 3.97 (s, 2H).

Workup

  1. extractionthe solution is extracted with AcOEt
  2. washThe organic layer is washed with H2O, and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ab6814d205234cc1b730d9edfbc76db5
Source dataset
uspto-grants-2012_06
Patent number
US08193349B2

Reaction notes

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