Methane → HCID 13537721, compound

HRID 1583960Notes

Reaction equation

HRID 1583960 reaction equation
C(C[C:4]([O:6][CH2:7]C)=[O:5])#N.C[O-:10].[Na+].[CH2:12]([O:14][CH:15]=[CH:16][C:17](=O)[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:13].Cl.C>C(OCC)(=O)C>[CH3:7][O:6][C:4]([C:18]1[C:19](=[O:20])[O:21][C:22]([CH3:23])=[C:16]([C:15]([O:14][CH2:12][CH3:13])=[O:10])[CH:17]=1)=[O:5]

Participants

7

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 10942334Sodium MethoxideHCID 54463595Ethyl ethoxymethyleneacetoacetate

Product 1

HCID 13537721HCID 13537721, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure described by Baker et al., Journ. of Chem. Soc. Perkin Trans. 1, 3, 677-685 (1979), ethyl cyanoacetate (3.5 g, 0.031 mol) was added to NaOMe solution (prepared from 0.72 g of sodium metal in 50 ml of MeOH), followed by 1 (5.77 g, 0.031 mol). The mixture was refluxed for 15 minutes, cooled and divided into two equal parts. The first portion was acidified with 2N HCl to pH 2-3 and extracted with CH2Cl2. The extracts were washed, dried over MgSO4, and evaporated to give an orange-colored solid. After decolorizing with Nuchar activated carbon in ethyl acetate and recrystallizing from EtOAc-hexane, white, fluffy crystals, of 3-(methoxycarbonyl)-5-(ethoxycarbonyl)-6-methyl-2-pyrone were obtained: 0.22 g, 6% yield; mp=94°-96° C.; NMR (DMSO-d6) δ 1.2-1.5 (t, 3H), 2.7 (s, 3H), 3.8 (s, 3H), 4.1-4.6 (q, 2H), 8.5 (s, 1H); IR (KBr) 1700-1730 cm-1 (C=O of Me and Et ester), 1770 cm-1 (C=O of pyrone).

Workup

  1. temperatureThe mixture was refluxed for 15 minutes
  2. temperaturecooled
  3. extractionextracted with CH2Cl2
  4. washThe extracts were washed
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customto give an orange-colored solid
  8. customrecrystallizing from EtOAc-hexane

Sources & evidence

ORD record
ord-1cd525638b754a4f98de16472d130173
Source dataset
uspto-grants-1985_11
Patent number
US04555517

Reaction notes

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