3-Methylbutanal → 1-(3,5,6-Trimethyl-2-pyrazinyl)-4-methyl-2-pentanol

HRID 1632272Notes

Reaction equation

HRID 1632272 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH3:9])=[N:4][C:3]=1[CH3:10].[CH:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14]>>[OH:16][CH:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[CH2:10][C:3]1[C:2]([CH3:1])=[N:7][C:6]([CH3:8])=[C:5]([CH3:9])[N:4]=1

Participants

3

Reactant 2

HCID 115523-MethylbutanalHCID 14296Tetramethylpyrazine

Product 1

HCID 5859411-(3,5,6-Trimethyl-2-pyrazinyl)-4-methyl-2-pentanolYield 60.7%

Procedure

The reaction of 13.6 grams (0.1 mole) of tetramethylpyrazine with 8.6 grams (0.1 mole) isovaleraldehyde was carried out in the manner described in Example II. The crude reaction mixture was washed with 50 milliliters of 6N HCl, and the aqueous layer was separated and washed with two 50 milliliter portions of methylene chloride. The acidic solution was neutralized with sodium carbonate and the oil that separated was dissolved in methylene chloride. The organic solution was dried over sodium sulfate, and the solvent was evaporated to give 13.5 grams of an oil. Distillation of the oil yielded 7.7 grams (35%) of product, b.p. 98°-100° C./0.05 mm Hg.

Workup

  1. customThe crude reaction mixture
  2. washwas washed with 50 milliliters of 6N HCl
  3. customthe aqueous layer was separated
  4. washwashed with two 50 milliliter portions of methylene chloride
  5. customthe oil that separated
  6. dissolutionwas dissolved in methylene chloride
  7. dry with materialThe organic solution was dried over sodium sulfate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4be9d2ffb8cd4a0db41b13ec462d81b9
Source dataset
uspto-grants-1984_10
Patent number
US04474819

Reaction notes

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