Potassium Iodide → 2-(2-Chloro-3-formyl-phenoxy)-butyronitrile

HRID 1254971ノート

反応式

HRID 1254971 の反応式
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].CS(O[CH:22]([CH2:25][CH3:26])[C:23]#[N:24])(=O)=O.[I-].[K+]>CN1CCCC1=O.O>[Cl:1][C:2]1[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=1[O:10][CH:22]([CH2:25][CH3:26])[C:23]#[N:24]

参加物

7

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 5933762-Chloro-3-hydroxybenzaldehydeHCID 154676912-(Methanesulfonyloxy)-butyronitrile2 回

生成物 1

HCID 595657782-(2-Chloro-3-formyl-phenoxy)-butyronitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
100 °C

実験手順

2-Chloro-3-hydroxy-benzaldehyde (1.0 g, 6.4 mmol) was dissolved in 10 ml N-methyl-pyrolidone at 20° C. The resultant yellow solution was degassed with argon. After addition of cesium carbonate (2.29 g, 7.0 mmol) the suspension was stirred for 20 minutes. 2-(methanesulfonyloxy)-butyronitrile (1.56 g, 9.6 mmol) and potassium iodide (0.05 g, 0.05 mmol) were then added and the reaction mixture was heated at 100° C. under microwave irradiation (Initiator™ Sixty, Biotage) for 3 minutes. After adding an additional portion of 2-(methanesulfonyloxy)-butyronitrile (0.52 g, 3.2 mmol) the reaction mixture was once again heated under microwave irradiation at 100° C. for 5 minutes. The reaction was monitored by TLC. On completion, the mixture was poured into water (0° C.) and extracted with ether. The organic layer was separated and washed with NaOH (1N), water and brine and dried with MgSO4. The crude material was purified on silicagel by flash chromatography (ethylacetate/cyclohexane) to give 2-(2-chloro-3-formyl-phenoxy)-butyronitrile as yellow oil; 1H-NMR (CDCl3) 1.25, t, 3H, 2.2 m, 2H, 4.81 dd, 1H, 7.4, m, 2H, 7.68 m, 1H, 10.5 s, 1H.

後処理

  1. customThe resultant yellow solution was degassed with argon
  2. temperaturewas once again heated under microwave irradiation at 100° C. for 5 minutes
  3. extractionextracted with ether
  4. customThe organic layer was separated
  5. washwashed with NaOH (1N), water and brine
  6. dry with materialdried with MgSO4
  7. customThe crude material was purified on silicagel by flash chromatography (ethylacetate/cyclohexane)

出典と根拠

ORDレコード
ord-e9d785fe21714a79a57a897c6af0118b
出典データセット
uspto-grants-2013_06
特許番号
US08455663B2

反応ノート

読み込み中…