Nitromethane → trans-4-Methoxy-beta-nitrostyrene

HRID 1685325ノート

反応式

HRID 1685325 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[N+:11]([CH3:14])([O-:13])=[O:12].[OH-].[Na+]>CO>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2](/[CH:1]=[CH:14]/[N+:11]([O-:13])=[O:12])=[CH:3][CH:4]=1

参加物

5

反応物 3

HCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 312444-Methoxybenzaldehyde

生成物 1

HCID 697963trans-4-Methoxy-beta-nitrostyrene

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a cool (0° C.), stirred solution of 4-anisaldehyde (1.75 mL, 14.3 mmol), nitromethane (2.0 mL, 36.9 mmol) in MeOH (6.0 mL) was added NaOH (1M, 40 mL), and allowed to warm to room temperature. After 2.5 hours, ice water was added with stirring, extracted with DCM (3×), the combined extracts were dried (MgSO4), filtered, concentrated and purified on Biotage Horizon to provide the product as a solid: 1H NMR (400 MHz, CDCl3) δ ppm: 7.97 (1H, d, J=13.64 Hz), 7.51 (1H, d, J=13.64 Hz), 7.50 (1H, d, J=8.84 Hz), 6.95 (2H, d, J=8.84 Hz), 3.86 (3H, s).

後処理

  1. temperatureto warm to room temperature
  2. extractionextracted with DCM (3×)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on Biotage Horizon

出典と根拠

ORDレコード
ord-347940af409348a9af43ff783f282a1a
出典データセット
uspto-grants-2012_04
特許番号
US08148400B2

反応ノート

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