Water → 4-Methoxy-3-(2,2,2-trifluoroethoxy)benzaldehyde

HRID 250706ノート

反応式

HRID 250706 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].I[CH2:13][C:14]([F:17])([F:16])[F:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:11][O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[O:1][CH2:13][C:14]([F:17])([F:16])[F:15]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12127IsovanillinHCID 677091,1,1-Trifluoro-2-iodoethane

生成物 1

HCID 126475004-Methoxy-3-(2,2,2-trifluoroethoxy)benzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

3-Hydroxy-4-methoxy-benzaldehyde (560, 2.9 g, 19.5 mmol), 2-iodo-1,1,1-trifluoroethane (561, 2.2 mL, 23 mmol), and potassium carbonate (3.7 g, 27 mmol) were dissolved in N,N-dimethylformamide (100 mL). The solution was stirred at 90° C. overnight under an atmosphere of nitrogen. The reaction was poured into water, extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The compound was isolated by silica gel column chromatography eluting with 25% to 50% ethyl acetate in hexanes to give white powder (562, 1.6 g, 40%).

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe compound was isolated by silica gel column chromatography
  7. washeluting with 25% to 50% ethyl acetate in hexanes
  8. customto give white powder (562, 1.6 g, 40%)

出典と根拠

ORDレコード
ord-d46fdbcebafe48f8b87f5cb67f20b137
出典データセット
uspto-grants-2011_01
特許番号
US07863288B2

反応ノート

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