Water → HCID 76576848, compound

HRID 1842079Notes

Reaction equation

HRID 1842079 reaction equation
[CH3:1][O:2][CH:3]([CH2:7][CH:8]=[CH2:9])[CH2:4][CH:5]=O.S(O)(O)(=O)=O.[NH2:15][OH:16].C([O-])(=O)C.[Na+].O>C(O)C>[CH3:1][O:2][CH:3]([CH2:7][CH:8]=[CH2:9])[CH2:4][CH:5]=[N:15][OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 159255Hydroxylamine, sulfate (1:1)HCID 517045Sodium AcetateHCID 57827767HCID 57827767, compound

Product 1

HCID 76576848HCID 76576848, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-methoxy-5-hexenal (3.0 g, contaminated with dichloromethane and triethylamine), hydroxylamine sulfate (990 mg) and sodium acetate (624 mg) in ethanol (6.5 mL)-water (0.65 mL) was stirred at room temperature for 12 hours. The reaction solution was poured into ice water, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography to obtain the title compound (500 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-548ed75a7f5548d4b070b6e9af9adc9b
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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