Water → 5-(1,1-Difluoroethyl)pyrazine-2-carboxylic acid

HRID 1524642Notes

Reaction equation

HRID 1524642 reaction equation
[F:1][C:2]([C:5]1[N:6]=[CH:7][C:8]([C:11]([O:13]C)=[O:12])=[N:9][CH:10]=1)([F:4])[CH3:3].O.O.[OH-].[Li+]>O1CCOCC1>[F:1][C:2]([C:5]1[N:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1)([F:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 66869779Methyl 5-(1,1-difluoroethyl)pyrazine-2-carboxylate

Product 1

HCID 668695495-(1,1-Difluoroethyl)pyrazine-2-carboxylic acidYield 19.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(1,1-difluoroethyl)pyrazine-2-carboxylate (0.65 g, approx. purity 85%) was dissolved in dioxan (2 mL) and water (2 mL) was added, followed by lithium hydroxide monohydrate (54 mg, portionwise). After stirring at RT for 90 mins, the mixture was concentrated to 2 mL and diethyl ether (20 mL) added. The mixture was then extracted with NaOH (1 N, aq., 20 mL), and the aqueous portions acidified with 6N HCl to pH 2. The aqueous portion was then extracted with EtOAc, dried over MgSO4 and evaporated to afford the title compound as a white solid (119 mg). 1H NMR (400 MHz, CDCl3) δ ppm 2.11 (t, J=18.8 Hz, 3H), 9.01 (d, J=1.3 Hz, 1H), 9.47 (d, J=1.3 Hz, 1H)

Workup

  1. concentrationthe mixture was concentrated to 2 mL and diethyl ether (20 mL)
  2. additionadded
  3. extractionThe mixture was then extracted with NaOH (1 N, aq., 20 mL)
  4. extractionThe aqueous portion was then extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-810b68a3441247adb4225d32ca38aa6a
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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