Potassium tert-butoxide → 2,2,6-Trimethylpyran-3,5-dione

HRID 341650Notes

Reaction equation

HRID 341650 reaction equation
CC(C)([O-])C.[K+].CO[C:9](=[O:19])[CH:10]([O:12][C:13]([CH3:18])([CH3:17])[C:14](=[O:16])[CH3:15])[CH3:11]>O1CCCC1>[CH3:18][C:13]1([CH3:17])[C:14](=[O:16])[CH2:15][C:9](=[O:19])[CH:10]([CH3:11])[O:12]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 595625612-(1,1-Dimethyl-2-oxopropoxy)propionic acid methyl ester

Product 1

HCID 595625492,2,6-Trimethylpyran-3,5-dioneYield 37.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of potassium tert-butoxide (28.5 g, 0.254 mol) in tetrahydrofuran (200 ml) cooled to 0° C., is added a solution of 2-(1,1-dimethyl-2-oxopropoxy)propionic acid methyl ester (24 g, 0.127 mol) in tetrahydrofuran (50 ml). The reaction mixture is stirred at 0° C. for 3 hours. The reaction mixture is quenched with ice cold water, and the aqueous phase is extracted with diethyl ether (3×200 ml). The organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2,2,6-trimethylpyran-3,5-dione (7.5 g) as a white solid.

Workup

  1. customThe reaction mixture is quenched with ice cold water
  2. extractionthe aqueous phase is extracted with diethyl ether (3×200 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe mixture is filtered
  6. customthe filtrate is evaporated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-33f0b148417f485cbe6e0bdaffb56dfd
Source dataset
uspto-grants-2014_11
Patent number
US08895761B2

Reaction notes

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