Sodium Acetate → O-Methyl-4-(2,4-dihydroxyphenyl)cyclohexanone Oxime

HRID 585688

反応式

HRID 585688 の反応式
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[C:16]([O-])(=O)C.[Na+].Cl.C[O:23][NH2:24]>C(O)C>[CH3:16][O:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][C:12](=[N:24][OH:23])[CH2:11][CH2:10]1

参加物

5

反応物 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 99424894-(2,4-Dihydroxyphenyl)cyclohexanone

生成物 1

HCID 86586322O-Methyl-4-(2,4-dihydroxyphenyl)cyclohexanone Oxime収率 47%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a round bottomed flask, equipped with magnetic stirrer was added 4-(2,4-dihydroxyphenyl)cyclohexanone (21 mg, 0.10 mmol), anhydrous ethanol (3 ml), sodium acetate (16 mg, 0.20 mmol) and O-methylhydroxylamine hydrochloride (9 mg, 0.22 mmol). The reaction mixture was heated under reflux for 6 hr, then partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was dried over anhydrous calcium sulphate, filtered and evaporated in vacuo furnishing a colourless oil. Purification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1, v/v), afforded the title compound as a white solid (11 mg, 47%). δH (CD3OD) 1.43-1.63 (2H, m), 1.81-1.92 (2H, m), 1.93-2.20 (2H, m), 2.24 (1H, dt), 2.38-2.44 (1H, m), 3.07 (1H, tt), 3.78 (3H, s), 6.20-6.23 (1H, m), 6.26 (1H, d), 6.85 (1H, d); m/z (ES−) 234.

後処理

  1. customTo a round bottomed flask, equipped with magnetic stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 6 hr
  4. custompartitioned between ethyl acetate (10 ml) and water (10 ml)
  5. dry with materialThe organic layer was dried over anhydrous calcium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customfurnishing a colourless oil
  9. customPurification via flash column chromatography (SiO2, ethyl acetate/petroleum ether, 1:1

出典と根拠

ORDレコード
ord-e0c7ab48a31f4390b8e8db4b22e5be2b
出典データセット
uspto-grants-2005_08
特許番号
US06933319B2

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