Hydroxylamine → HCID 76979141, compound

HRID 1695421Notes

Reaction equation

HRID 1695421 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.[NH2:9][OH:10].C([O-])(=O)C.[Na+]>C(O)C.O>[O:1]1[CH2:6][CH2:5][CH:4]([CH:7]=[N:9][OH:10])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 787HydroxylamineHCID 517045Sodium AcetateHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehyde

Product 1

HCID 76979141HCID 76979141, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of tetrahydro-pyran-4-carbaldehyde (36.9 g, 259 mmol) and hydroxylamine (27.2 g, 388 mmol) in ethanol (246 mL) and water (246 mL) was added sodium acetate (42.9 g, 517 mmol) and the resulting mixture heated at 90° C. overnight. After cooling to room temperature the resulting mixture was then evaporated and extracted with diethylether and water. The organic extract was then washed with water, brine, dried over sodium sulfate and evaporated. Purification by chromatography (silica, heptane:ethyl acetate=1:1) afforded the title compound (16.8 g, 50%) which was obtained as a yellow liquid. MS: m/e=129.1 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the resulting mixture
  2. customwas then evaporated
  3. extractionextracted with diethylether and water
  4. extractionThe organic extract
  5. washwas then washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customPurification by chromatography (silica, heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-311d8929f7774c16abb6b78640db8167
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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