2-Chloroethanol → HCID 14881369, compound

HRID 2352604Notes

Reaction equation

HRID 2352604 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-9f6fffc6d818439ca93af3c78c859447
Source dataset
uspto-grants-1989_10
Patent number
US04877875

Reaction notes

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