Nitromethane → 3-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol

HRID 1627331ノート

反応式

HRID 1627331 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[F-].[K+].[CH3:18][N+:19]([O-:21])=[O:20]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([CH3:15])([CH3:14])[CH:12]([OH:13])[CH2:18][N+:19]([O-:21])=[O:20])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

5

反応物 3

HCID 6375NitromethaneHCID 522689Potassium FluorideHCID 592591132-(3,4-Dimethoxyphenyl)-2-methylpropanal

生成物 1

HCID 667407963-(3,4-Dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol収率 97%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2-(3,4-dimethoxyphenyl)-2-methylpropanal (1.0 g, 4.8 mmol) in EtOH (30 mL) were added KF (335 mg, 5.8 mmol) and CH3NO2 (1.56 mL, 28.8 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated, diluted with EtOAc, and washed with brine. The organic layer was dried over MgSO4, filtered and concentrated to give 3-(3,4-dimethoxyphenyl)-3-methyl-1-nitrobutan-2-ol (1.25 g, 97%). 1H NMR (400 MHz, CDCl3) δ 6.91-6.84 (m, 3H), 4.44 (m, 1H), 4.24 (d, 2H), 3.90 (s, 3H), 3.88 (s, 3H), 2.38 (d, 1H), 1.40 (s, 3H), 1.38 (s, 3H).

後処理

  1. concentrationThe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-f24fcd48f1c94012aebd3d4e53406754
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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