Tetrahydrofuran → HCID 66832323、化合物

HRID 562415ノート

反応式

HRID 562415 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](Cl)(Cl)=[O:9])=[CH:4][CH:3]=1.[CH:12]([Mg]Br)=[CH2:13].[Cl-].[NH4+].[CH2:18]1COC[CH2:19]1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([P:8](=[O:9])([CH:12]=[CH2:13])[CH:18]=[CH2:19])=[CH:4][CH:3]=1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 25517Ammonium ChlorideHCID 12670632(4-Fluorophenyl)phosphonic dichlorideHCID 178418507HCID 178418507、化合物

生成物 1

HCID 66832323HCID 66832323、化合物収率 83%

反応条件

温度
-70 °C

実験手順

4-Fluorophenyl-phosphonic dichloride (6.86 g, 32.2 mmol) was dissolved in dry THF (50 mL), placed under a nitrogen atmosphere, and chilled to −70° C. To this stirred solution was added dropwise a solution of vinyl magnesium bromide in THF (80.5 mL, 1M). The resulting solution was stirred for 90 minutes at −70° C. An aqueous solution of ammonium chloride (500 mL, 2M) was chilled to 0° C. and stirred rapidly while the cold reaction mixture was added. The product was extracted into dichloromethane and washed with saturated aqueous sodium bicarbonate followed by water. The organic phase was dried with sodium sulfate, filtered, and concentrated by rotary evaporation to yield 5.214 g of 4-fluoro-phenyl-divinyl-phosphine oxide (26.6 mmol, 83%) as a white solid. 1H NMR (400 MHz, CDCl3) 7.80-7.71 (m, 2H); 7.25-7.18 (m 2H); 6.56-6.22 (m, 6H); ESMS (m/z): (M+1)+ found, 197.

後処理

  1. stirringstirred rapidly while the cold reaction mixture
  2. additionwas added
  3. extractionThe product was extracted into dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-d336d5d68b4c4907a03c4ece191ebd93
出典データセット
uspto-grants-2011_11
特許番号
US08067395B2

反応ノート

読み込み中…