Ethanol → 4-(Pyrazin-2-yl)benzaldehyde

HRID 2416563Notes

Reaction equation

HRID 2416563 reaction equation
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[CH:16]=[N:15][CH:14]=[CH:13][N:12]=1.[CH:17]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)=[O:18]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:12]1[CH:13]=[CH:14][N:15]=[CH:16][C:11]=1[C:22]1[CH:23]=[CH:24][C:19]([CH:17]=[O:18])=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 73277ChloropyrazineHCID 5910734-Formylphenylboronic Acid

Product 1

HCID 38535194-(Pyrazin-2-yl)benzaldehydeYield 42.2%

Reagents, catalysts & solvents 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution 15 of 2-chloropyrazine (2.30 g, 20.06 mmol), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.56 g (42%) of 4-pyrazinylbenzaldehyde.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b36cc7482a2f4a4b897b455db28a481c
Source dataset
uspto-grants-2004_11
Patent number
US06825172B2

Reaction notes

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