Sulfuric Acid → 2-(3,4-Dihydroxybutyl)pyrazine

HRID 980473Notes

Reaction equation

HRID 980473 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[CH2:7]CC=C.[Mn]([O-])(=O)(=O)=O.[K+].OS(O)(=O)=O.[OH2:22].[CH3:23][C:24]([CH3:26])=[O:25]>O>[OH:25][CH:24]([CH2:26][OH:22])[CH2:23][CH2:7][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 18366337Propan-2-one--water (1/1)HCID 22477625Pyrazine, 3-butenyl-

Product 1

HCID 202216172-(3,4-Dihydroxybutyl)pyrazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

4.15 g of 4-(2-pyrazinyl)-1-butene (1300) was dissolved in 100 ml of 1:1 water/acetone and cooled to 5° C. To this was slowly added a solution of 3.60 g of potassium permanganate in 300 ml of water. This was kept at 5° C. for 18 hours and then allowed to stir for 4 hours at R.T. It was adjusted to pH 7 with 5% H2SO4, filtered through celite and concentrated. Continuous extraction with chloroform for 2 days followed by evaporation of the solvent left 4.27 g of product (1400) which was distilled under vacuum, b.p. 174°-5° (0.2 mm). UV H2O max: 268 (3.76), 272 (3.76).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated
  3. extractionContinuous extraction with chloroform for 2 days
  4. customfollowed by evaporation of the solvent
  5. waitleft 4.27 g of product (1400) which
  6. distillationwas distilled under vacuum, b.p. 174°-5° (0.2 mm)

Sources & evidence

ORD record
ord-c86746fcab3b431386b33e44e93f4462
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Reaction notes

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