Diethyl Ether → HCID 15386524, compound

HRID 2395225Notes

Reaction equation

HRID 2395225 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5]O[C:3]=1[CH3:9].[CH2:10]([O:12][C:13](=[O:16])[CH2:14][NH2:15])[CH3:11].[OH-].[Na+].C(OCC)C>C(O)C.CC(C)=O>[CH2:10]([O:12][C:13]([CH2:14][N:15]1[CH:5]=[CH:6][C:7](=[O:8])[C:2]([OH:1])=[C:3]1[CH3:9])=[O:16])[CH3:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8369MaltolHCID 12176Glycine ethyl esterHCID 14798Sodium Hydroxide

Product 1

HCID 15386524HCID 15386524, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

3-hydroxy-2-methyl-4-pyrone (15 g) in ethanol (250 ml) has added to it glycine-ethyl ester (14 g) and concentrated aqueous sodium hydroxide to adjust pH to 10.0, the mixture is stirred at room temperature for several days, then rotary evaporated to dryness, resulting in white residue. Dissolution in acetone followed by di-ethyl ether treatment yields white precipitate of 1-ethoxycarbonylmethyl-3-Hydroxy-2-methyl-pyrid-4-one. The molecular ion mass M+=266.7. The compound dissolved in ethanol/water mixture with added iron forms the purple coloured complex. TLC showed a single, purple band separate and of lower rf than the 3-hydroxy-2-methyl-4-pyrone control (orange-red).

Workup

  1. customrotary evaporated to dryness
  2. customresulting in white residue

Sources & evidence

ORD record
ord-b4eb4e0d10ed41bb85fe12646907056e
Source dataset
uspto-grants-1998_09
Patent number
US05814614

Reaction notes

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