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

HRID 1862447Notes

Reaction equation

HRID 1862447 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]>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

5

Reactant 2

HCID 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 EtherSolventHCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide in tert-butanol (1 M, 203 mL) and the product from Example 44B (15.5 g, 97 mmol) in ether (55 mL) were processed as described in Example 43C. The residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (200:1:1:200) provided the title compound. 1H NMR (CDCl3) δ 1.48 (d, 3H), 3.43 (d, 1H), 3.92 (d, 1H), 3.97 (q, 1H), 4.04 (d, 1H), 4.44 (d, 1H).

Workup

  1. customThe residue was purified on silica gel eluting with ethyl acetate:formic acid:water:hexane (200:1:1:200)

Sources & evidence

ORD record
ord-cc7df6c706fb4b2ba3e108b6efc09c26
Source dataset
uspto-grants-2003_03
Patent number
US06538004B2

Reaction notes

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