Hydrochloric Acid → 2-methyl-2H-pyran-3,5(4H,6H)-dione

HRID 478304Notes

Reaction equation

HRID 478304 reaction equation
CC(C)([O-])C.[K+].[CH3:7][CH:8]([O:12][CH2:13][C:14]([O:16]C)=O)[C:9](=[O:11])[CH3:10].Cl>C(O)(C)(C)C.CCOCC>[CH3:7][CH:8]1[C:9](=[O:11])[CH2:10][C:14](=[O:16])[CH2:13][O:12]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 71360827Methyl (1-methyl-2-oxopropoxy)acetate

Product 1

HCID 234974742-methyl-2H-pyran-3,5(4H,6H)-dione

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

A mechanically stirred solution of potassium tert-butoxide in tert-butanol (1 M, 203 mL) under a nitrogen atmosphere was treated with anhydrous ether (125 mL), cooled to 0° C., treated with the product from Example 84B (15.5 g, 97 mmol) in ether (55 mL) over 2 minutes, stirred for 10 minutes and then treated with 2M HCl (240 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×, 200 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. The residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (200:1:1:200) to provide the title compound.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×, 200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (200:1:1:200)

Sources & evidence

ORD record
ord-dfd519c5d71d45d4abf893a9c116b05b
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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