Sodium Hydroxide → HCID 59253231, compound

HRID 386888Notes

Reaction equation

HRID 386888 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([CH3:14])([CH3:13])[C:8](=O)[CH2:9][C:10]#[N:11].[OH-:15].[Na+].S(O)(O)(=O)=O.[NH2:22]O>O>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]([C:8]1[CH:9]=[C:10]([NH2:11])[O:15][N:22]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159255Hydroxylamine, sulfate (1:1)HCID 59253251HCID 59253251, compound

Product 1

HCID 59253231HCID 59253231, compoundYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 5-(2-methoxy-ethoxy)-4,4-dimethyl-3-oxo-pentanenitrile (3.04 g, 15.27 mmol) and sodium hydroxide (1.31 g, 32.82 mmol) in water (34 mL) is added hydroxylamine sulfate (1.25 g, 7.63 mmol). The reaction mixture is stirred at reflux for 18 h. After this time, the reaction mixture is cooled to room temperature and extracted with ethyl acetate 3 times. The organic layers are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel using methanol/DCM provides the title compound. Yield: 35.8%. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.30 (6H, s), 3.39 (3H, s), 3.50 (2H, s), 3.50-3.57 (2H, m), 3.57-3.62 (2H, m), 3.30-4.50 (2H, br), 5.16 (1H, s).

Workup

  1. temperatureat reflux for 18 h
  2. extractionextracted with ethyl acetate 3 times
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8264371b99844445b2a9413bbea3ccf1
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

Loading…