2-Chloroethanol → HCID 14881158, compound

HRID 1608333Notes

Reaction equation

HRID 1608333 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]([CH2:19][CH3:20])=[C:8]([CH2:21][CH3:22])[N:7]=1.[OH-].[Na+]>C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]([CH2:21][CH3:22])=[C:9]([CH2:19][CH3:20])[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

5

Reactant 3

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 178437784HCID 178437784, compound

Product 1

HCID 14881158HCID 14881158, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (20.15 g, 0.25M) was added to a solution of 2-hydroxy-3-benzyl-5,6-diethyl-pyrazine (12.10 g, 50 mM) and 5N NaOH (50 ml) in t-butanol (150 ml), and stirred at 60° C. for 3 hours. The t-butanol was distilled off in vacuo, water was added thereto and the mixture was extracted three times with chloroform. The extract was dried with anhydrous magnesium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 230 g) packed with chloroform and eluted with chloroform-methanol (100:1) to obtain compound 640 (12.31 g, yield: 58.7%).

Workup

  1. distillationThe t-butanol was distilled off in vacuo, water
  2. additionwas added
  3. extractionthe mixture was extracted three times with chloroform
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica-gel (C-200, 230 g)
  7. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-a2728d4b796e4b6ea566811d11c73962
Source dataset
uspto-grants-1989_09
Patent number
US04870176

Reaction notes

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