Potassium tert-butoxide → 2,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

HRID 478294Notes

Reaction equation

HRID 478294 reaction equation
CC(C)([O-])C.[K+].[CH3:7][C:8]([CH3:18])([O:12][CH2:13][C:14](OC)=[O:15])[C:9](=[O:11])[CH3:10]>C(OCC)C>[CH3:7][C:8]1([CH3:18])[C:9](=[O:11])[CH2:10][C:14](=[O:15])[CH2:13][O:12]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 85791200Methyl 2-(1,1-dimethyl-2-oxopropoxy)acetate

Product 1

HCID 140728872,2-dimethyl-2H-pyran-3,5(4H,6H)-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of potassium tert-butoxide (1M in tert-butanol, 12.1 mL, 12.1 mmol) in diethyl ether (7.5 mL) at 0° C. under N2 gas was treated with a solution of the product from Example 66B in diethyl ether (3 mL). After 10 minutes, the reaction mixture was quenched into 2N HCl (25 mL) and extracted with diethyl ether (3×25 mL). The organic layers were combined, washed with brine, dried over Na2SO4, concentrated to an oil, treated with 10% dichloromethane in hexane (5 mL), and placed in the freezer for 1 hour. The resulting crystals were collected by filtration, washed with a cold solution of 10% dichloromethane in hexane, and dried to provide the title compound (431 mg).

Workup

  1. customthe reaction mixture was quenched into 2N HCl (25 mL)
  2. extractionextracted with diethyl ether (3×25 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. additiontreated with 10% dichloromethane in hexane (5 mL)
  7. waitplaced in the freezer for 1 hour
  8. filtrationThe resulting crystals were collected by filtration
  9. washwashed with a cold solution of 10% dichloromethane in hexane
  10. customdried

Sources & evidence

ORD record
ord-4c45c51cb5f74bb38ed1951dd5c0599e
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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