Hydrochloric Acid → 6-Fluoro-3-methoxypyrazine-2-carbaldehyde

HRID 606189Notes

Reaction equation

HRID 606189 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl.O>ClCCl>[F:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]([O:12][CH3:13])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 22247880HCID 22247880, compound

Product 1

HCID 222483286-Fluoro-3-methoxypyrazine-2-carbaldehydeYield 65.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

After dissolving 447 mg of methyl 6-fluoro-3-methoxypyrazine-2-carboxylate in 8 ml of dichloromethane, the solution was cooled to −78° C. Next, 1.76 ml of diisobutylaluminium hydride (1.5 M, toluene solution) was added dropwise and the mixture was stirred for 30 minutes. After adding 10 ml of 1N hydrochloric acid dropwise to the reaction solution, water was added and extraction was performed with dichloromethane. After then drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (245 mg, 65% yield).

Workup

  1. additionwas added
  2. extractionextraction
  3. dry with materialAfter then drying over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fe0a6518e77c4f5db69795fb68941350
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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