Triethylamine → HCID 23462043, compound

HRID 2286700Notes

Reaction equation

HRID 2286700 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[N:7][C:6]([CH3:9])=[CH:5][N:4]=1.C(N(CC)CC)C.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]>C1C=CC=CC=1>[C:17]([O:1][CH2:2][C:3]1[CH:8]=[N:7][C:6]([CH3:9])=[CH:5][N:4]=1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 5800615-Methyl-2-pyrazinemethanol

Product 1

HCID 23462043HCID 23462043, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 2-hydroxymethyl-5-methylpyrazine (6.2 g) and triethylamine (6.4 ml) in anhydrous benzene (150 ml) dropwise addition was made of a solution of pivaloyl chloride (6.15 ml) in anhydrous benzene (50 ml). The solution was maintained at boiling for 7 hours, the solvent was then evaporated and the residue treated with acetone. After filtration of the insoluble solid, the filtrate was evaporated to dryness and the residue re-dissolved in chloroform. The chloroform solution was first dehydrated and then evaporated to dryness, obtaining 7 g (71.5%) of 5-methyl-2-pyrazinylmethyl pivalate, b.p.=74° C./0.1 mmHg.

Workup

  1. temperatureThe solution was maintained
  2. customthe solvent was then evaporated
  3. additionthe residue treated with acetone
  4. filtrationAfter filtration of the insoluble solid
  5. customthe filtrate was evaporated to dryness
  6. dissolutionthe residue re-dissolved in chloroform
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d264a38a797541b085380ef383a4575e
Source dataset
uspto-grants-1981_05
Patent number
US04267327

Reaction notes

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