2-Chloroethanol → HCID 14881369, compound

HRID 1904338Notes

Reaction equation

HRID 1904338 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[C:15]([CH2:16][CH3:17])=[N:14][C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[N:7]=1.[OH-].[Na+]>C(O)(C)(C)C>[OH:3][CH2:2][CH2:1][N:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[N:14]=[C:15]([CH2:16][CH3:17])[C:6]1=[O:5]

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 14798Sodium HydroxideHCID 178437529HCID 178437529, compound

Product 1

HCID 14881369HCID 14881369, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorohydrin (20.2 g, 0.25M) was added to a solution of 2-hydroxy-3-ethyl-5,6,7,8-tetrahydro quinoxaline (8.90 g, 50 mM) in dilute aqueous 5N NaOH (50 ml) and t-butanol (150 ml), and stirred at 60° C. for 3 hours. The t-butanol was distilled off in vacuo. Water was added to the residue, which residue was then extracted three times with chloroform, dried with anhydrous sodium sulfate and concentrated in vacuo. The residue was charged on a column of silica-gel (C-200, 170 g) packed with chloroform, and eluted with chloroform-methanol (100:1) to obtain compound 646 (9.30 g, yield: 83.8%).

Workup

  1. distillationThe t-butanol was distilled off in vacuo
  2. additionWater was added to the residue, which residue
  3. extractionwas then extracted three times with chloroform
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica-gel (C-200, 170 g)
  7. washeluted with chloroform-methanol (100:1)

Sources & evidence

ORD record
ord-0233683736604386a417ff12e97b49d3
Source dataset
uspto-grants-1989_06
Patent number
US04837319

Reaction notes

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