Acetic Acid → 1-hydroxypropan-2-one O-tetrahydro-2H-pyran-2-yl oxime

HRID 82774

Reaction equation

HRID 82774 reaction equation
[OH:1][CH2:2][C:3](=O)[CH3:4].[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][NH2:13].C(O)(=O)C>CO.N1C=CC=CC=1>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:12][N:13]=[C:3]([CH3:4])[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8299HydroxyacetoneHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

Product 1

HCID 866397851-hydroxypropan-2-one O-tetrahydro-2H-pyran-2-yl oximeYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A mixture of 1-hydroxypropan-2-one (1 g, 13.5 mmol) and O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (1.9 g, 16.2 mmol) in methanol (20 mL) and pyridine (7 mL) was treated with acetic acid (0.23 mL, 4 mmol) and stirred at room temperature for 12 hours. The mixture was then concentrated under reduced pressure. The residue was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organic extract was concentrated and purified by chromatography (SiO2, eluted with EtOAc-hexane-2:1) to afford 1.8 g of the title compound. MS (DCI/NH3) m/z 174 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. additionThe residue was diluted with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. custompurified by chromatography (SiO2, eluted with EtOAc-hexane-2:1)

Sources & evidence

ORD record
ord-6038ac03e83941fcb32f3894dbb584ae
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Linked notes

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