Sodium Hydroxide → HCID 12648557, compound

HRID 908344Notes

Reaction equation

HRID 908344 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][C:5](=NOCC(O)=O)[C:6]1[CH:10]=[CH:9][S:8][CH:7]=1.[OH-].[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=[O:21].[K+].[K+]>O>[CH3:17][C:2]1([CH3:1])[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:21])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24412Potassium PersulfateHCID 85442666HCID 85442666, compound

Product 1

HCID 12648557HCID 12648557, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(4-Methyl-1-thiophen-3-yl-pentylideneaminooxy)-acetic acid (2.17 g, 8.5 mmol) was added to a 0.1 M sodium hydroxide solution (93.5 ml) and heated to reflux. A solution of potassium persulfate (3.45 g, 12.75 mmol) in water (10 ml) was added dropwise and heating continued. After 2 hours, the reaction mixture was extracted with dry diethyl ether (100 ml). The organic layer was then washed with saturate sodium bicarbonate, water and brine, dried (Na2SO4) and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to afford the title compound as a colourless oil (196 mg, 13%). MS (ES+) 18. δH (d6DMSO): 1.42 (6H, s), 2.03 (2H, t), 2.60 (2H, t), 7.22 (1H, d), 7.42 (1H, d).

Workup

  1. temperatureheated to reflux
  2. temperatureheating
  3. extractionthe reaction mixture was extracted with dry diethyl ether (100 ml)
  4. washThe organic layer was then washed with saturate sodium bicarbonate, water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-aaa1b744e3de49e392194a17bc9b9ee2
Source dataset
uspto-grants-2011_09
Patent number
US08017619B2

Reaction notes

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