Water → 5-(Fluoromethyl)pyrazine-2-carboxylic acid

HRID 1429628Notes

Reaction equation

HRID 1429628 reaction equation
[F:1][CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([O:11]C)=[O:10])=[N:7][CH:8]=1.O.O.[OH-].[Li+].CCOCC>O1CCOCC1>[F:1][CH2:2][C:3]1[N:4]=[CH:5][C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 168937Lithium hydroxide, monohydrateHCID 699365032-Pyrazinecarboxylic acid, 5-(fluoromethyl)-, methyl ester

Product 1

HCID 668695845-(Fluoromethyl)pyrazine-2-carboxylic acidYield 82.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-(fluoromethyl)pyrazine-2-carboxylate (94 mg) was dissolved in dioxan (1 mL) and water (1 mL) was added, followed by lithium hydroxide monohydrate (60 mg). After stirring at RT for 18 h, Et2O (20 mL) was added and the mixture was then extracted with NaOH (1 N, aq., 2×20 mL). The aqueous portions were acidified with 6N HCl to pH 1, extracted with EtOAc (2×40 mL), the combined organic portions dried over MgSO4 and evaporated to afford the title compound as a white solid (71 mg). 1H NMR (400 MHz, CDCl3) δ ppm 5.70 (d, J=46.2 Hz, 2 H), 8.85 (s, 1 H), 9.40 (s, 1 H)

Workup

  1. extractionthe mixture was then extracted with NaOH (1 N, aq., 2×20 mL)
  2. extractionextracted with EtOAc (2×40 mL)
  3. dry with materialthe combined organic portions dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-c7ab1ec0a473411b8513c0c6eab8e12a
Source dataset
uspto-grants-2015_01
Patent number
US08940734B2

Reaction notes

Loading…