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

HRID 82774

反応式

HRID 82774 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1049Pyridine溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6038ac03e83941fcb32f3894dbb584ae
出典データセット
uspto-grants-2014_09
特許番号
US08846730B2

関連ノート

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