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

HRID 82774

반응식

HRID 82774 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6038ac03e83941fcb32f3894dbb584ae
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846730B2

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