Phosphate → 2,2-Diphenylbutyronitrile

HRID 2119432ノート

反応式

HRID 2119432 の反応式
[Li+].[CH3:2][CH:3]([N-]C(C)C)C.[C:9]1([CH:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]#[N:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Br)C.P([O-])([O-])([O-])=O>C1COCC1>[C:18]1([C:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)([CH2:2][CH3:3])[C:16]#[N:17])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 1061PhosphateHCID 6332Ethyl BromideHCID 6837DiphenylacetonitrileHCID 2724682Lithium diisopropylamide

生成物 1

HCID 796782,2-Diphenylbutyronitrile収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-30 °C

実験手順

173 ml (0.259 mol) of a 1.5 M solution of LDA in THF were added dropwise to a solution of 50.0 g (0.259 mol) of diphenylacetonitrile in 500 ml of THF (abs.) at −78° C. under argon, and the mixture was then stirred at −30° C. for one hour. Then, at −78° C., 28.23 g (0.259 mol) of ethyl bromide were added. The mixture was allowed to reach room temperature and was stirred for 16 hours. Subsequently, 80 ml of phosphate buffer (pH 7) were added and the mixture was evaporated. The residue was taken up in water and extracted three times with ethyl acetate. The combined organic phases were dried over MgSO4, and the solvent was stripped off under reduced pressure. The crude product was chromatographed on silica gel with n-heptane/acetic acid (20:1). 38.2 g (67%) of 2,2-diphenylbutyronitrile were obtained.

後処理

  1. customto reach room temperature
  2. stirringwas stirred for 16 hours
  3. customthe mixture was evaporated
  4. extractionextracted three times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. customThe crude product was chromatographed on silica gel with n-heptane/acetic acid (20:1)

出典と根拠

ORDレコード
ord-2e9dddc2c9dd481f85f618ab7c421073
出典データセット
uspto-grants-2004_02
特許番号
US06686369B1

反応ノート

読み込み中…