2-Chloroethanol → HCID 14881121, compound

HRID 1608330Notes

Reaction equation

HRID 1608330 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]([CH3:19])=[C:8]([CH3:20])[N:7]=1.[OH-].[Na+].O>C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]([CH3:20])=[C:9]([CH3:19])[N:10]=[C:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=[O:5]

Participants

6

Reactant 4

HCID 342-ChloroethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 178433445HCID 178433445, compound

Product 1

HCID 14881121HCID 14881121, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (4.03 g, 50 mM) was added to a solution of 2-hydroxy-3-benzyl-5,6-dimethyl-pyrazine (2.14 g, 10 mM) and 5N NaOH (10 ml) in t-butanol (30 ml), and stirred at 60° C. for 2.5 hours. Water (100 ml) was added to the reaction mixture, and the mixture was extracted three times with chloroform, the extract dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 25 g) and eluted with chloroform-methanol (100:1) to obtain compound 112 (2.22 g, yield: 86.0%).

Workup

  1. extractionthe mixture was extracted three times with chloroform
  2. dry with materialthe extract dried with anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. additionThe residue was charged on a column of silica-gel (C-200, 25 g)
  5. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-10e099ae4cc54cec862a158bd9d4e193
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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