Water → 5-Ethoxypyrazine-2-carboxylic acid

HRID 1524641Notes

Reaction equation

HRID 1524641 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([O:12]CC)=[O:11])=[N:8][CH:9]=1)[CH3:2].O.O.[OH-].[Li+].C([O-])(O)=O.[Na+]>O1CCOCC1.C(OCC)C>[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]([C:10]([OH:12])=[O:11])=[N:8][CH:9]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516892Sodium BicarbonateHCID 668696851262803-60-0

Product 1

HCID 574756925-Ethoxypyrazine-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-ethoxypyrazine-2-carboxylate (0.65 g, approx. purity 85%) was dissolved in dioxan (3 mL) and water (3 mL) was added, followed by lithium hydroxide monohydrate (255 mg, portionwise over 10 mins). After stirring at RT for 24 h, diethyl ether (25 mL) and NaHCO3 (sat., aq., 25 mL) were added. The layers were separated and the organic layer was extracted with NaOH (1 N, aq., 25 mL). The combined aqueous portions were acidified with 6N HCl to pH 2, and the mixture extracted with EtOAc (3×40 mL). The combined EtOAc extracts were dried over MgSO4 and evaporated to afford the title compound as an off-white powder. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (t, J=7.1 Hz, 3H), 4.53 (q, J=7.1 Hz, 2H), 8.16 (d, J=1.2 Hz, 1H), 8.98 (d, J=1.2 Hz, 1H)

Workup

  1. customThe layers were separated
  2. extractionthe organic layer was extracted with NaOH (1 N, aq., 25 mL)
  3. extractionthe mixture extracted with EtOAc (3×40 mL)
  4. dry with materialThe combined EtOAc extracts were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-3d6b578abcc34367830e71e30b45624c
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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