1,4-Dioxane → HCID 15027354, compound

HRID 1195863Notes

Reaction equation

HRID 1195863 reaction equation
[OH:1][NH:2][CH2:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.CC([O-])=[O:19].[Na+].[O:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>O>[CH:5]1[C:6]2[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]=2[CH:15]=[CH:16][C:4]=1[CH2:3][N:2]([C:24](=[O:25])[C:23]([O:22][CH2:27][CH3:26])=[O:19])[OH:1]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 517045Sodium AcetateHCID 15027353HCID 15027353, compound

Product 1

HCID 15027354HCID 15027354, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

The crude hydroxylamine (4.2 g, 0.02 mol) from Example 1 is dissolved in dioxane (80 ml) and water (50 ml). The turbid solution is cooled to -5° C. and then treated with NaOAc (3.3 g, 0.04 mol) followed by ethyl oxalylchloride (3.0 g, 0.022 mol). The mixture is stirred at 24° C. for 3.0 hours, poured onto ice-1N HCl (40 mL) and extracted with CH2Cl2. The extract is washed with brine, water and dried over Na2SO4. The solvent is distilled off to give (9H-fluoren-2-ylmethyl)hydroxyamino-oxo-acetic acid, ethyl ester which is fractionally recrystallized from isopropyl ether and CH2Cl2 and then from isopropyl ether. Yield 1.6 g (26%); mp 130°-131° C.

Workup

  1. additionpoured onto ice-1N HCl (40 mL)
  2. extractionextracted with CH2Cl2
  3. washThe extract is washed with brine, water
  4. dry with materialdried over Na2SO4
  5. distillationThe solvent is distilled off

Sources & evidence

ORD record
ord-69ecdf80ac864a478165e7bc6f918bd3
Source dataset
uspto-grants-1992_05
Patent number
US05112846

Reaction notes

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