Ethylene → HCID 14881362, compound

HRID 2352617Notes

Reaction equation

HRID 2352617 reaction equation
[CH2:1]=[CH2:2].[OH:3][C:4]1[C:13]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]=1.[OH-:22].[Na+]>C(O)(C)(C)C>[OH:22][CH2:1][CH2:2][N:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[N:12]=[C:13]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]1=[O:3]

Participants

5

Reactant 3

HCID 6325EthyleneHCID 14798Sodium HydroxideHCID 178517341HCID 178517341, compound

Product 1

HCID 14881362HCID 14881362, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

Ethylene chlorodrohydrin (9.0 g) was added to a solution of 2-hydroxy-3-(2-phenylethyl)-5,6,7,8-tetrahydroquinoxaline (5.59 g, 22 mM) in aqueous 5N NaOH and t-butanol (60 ml), and stirred at 60° C. for 3 hours. The t-butanol was distilled off in vacuo, water was added to the residue, and the mixture was extracted three times with chloroform. The extract was 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 (200:1) to obtain compound 645 (6.73 g, yield: 90.9%).

Workup

  1. distillationThe t-butanol was distilled off in vacuo, water
  2. additionwas added to the residue
  3. extractionthe mixture was extracted three times with chloroform
  4. dry with materialThe extract was dried 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 (200:1)

Sources & evidence

ORD record
ord-a32b8a109411471eaa3d9e1aec7e580b
Source dataset
uspto-grants-1989_10
Patent number
US04877877

Reaction notes

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