Acetic Acid → HCID 87087465, compound

HRID 1931099Notes

Reaction equation

HRID 1931099 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>N1C=CC=CC=1.CO>[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 87087465HCID 87087465, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

To a solution 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 pyridine (7 mL) and methanol (20 mL) was added acetic acid (0.23 mL, 4 mmol) and the resulting mixture was stirred at room temperature for 12 hours. The mixture was then concentrated under reduced pressure and the residue was treated with a saturated solution of NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography (EtOAc-Hexanes 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 treated with a saturated solution of NaHCO3
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography (EtOAc-Hexanes 2:1)

Sources & evidence

ORD record
ord-827fc78d538e47e18b6c95c00843e008
Source dataset
uspto-grants-2012_05
Patent number
US08188135B2

Reaction notes

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