2-Chloroethanol → HCID 14881217, compound

HRID 1904331Notes

Reaction equation

HRID 1904331 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:11]([CH2:12][CH3:13])=[N:10][C:9]([CH3:14])=[C:8]([CH3:15])[N:7]=1.[OH-].[Na+].C([O-])([O-])=O.[K+].[K+]>C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]([CH3:15])=[C:9]([CH3:14])[N:10]=[C:11]([CH2:12][CH3:13])[C:6]1=[O:5]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 178437623HCID 178437623, compound

Product 1

HCID 14881217HCID 14881217, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (32.21 g, 0.4M) was added to a solution of 2-hydroxy-3-ethyl-5,6-dimethyl-pyrazine (12.16 g, 80 mM) and 5N NaOH (80 ml) in t-butanol (240 ml), and stirred at 60° C. for 3 hours. Dilute aqueous K2CO3 was added to the reaction mixture, the mixture extracted with chloroform, and the resultant aqueous layer extracted twice with further chloroform. The combined chloroform layers were dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 250 g) packed with chloroform and eluted with chloroform-methanol form-methanol (from 200:1 to 50:1) to obtain compound 630 (12.31 g, yield: 78.5%).

Workup

  1. extractionthe mixture extracted with chloroform
  2. extractionthe resultant aqueous layer extracted twice with further chloroform
  3. dry with materialThe combined chloroform layers were dried with anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. additionThe residue was charged on a column of silica-gel (C-200, 250 g)
  6. washeluted with chloroform-methanol form-methanol (from 200:1 to 50:1)

Sources & evidence

ORD record
ord-b22c1990747d4a368021e38be49fad4a
Source dataset
uspto-grants-1989_06
Patent number
US04837319

Reaction notes

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