Water → 5,5-Diphenylpent-4-enenitrile

HRID 1741770ノート

反応式

HRID 1741770 の反応式
[C-:1]#[N:2].[Na+].Br[CH2:5][CH2:6][CH:7]=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C)P(N(C)C)(N(C)C)=O>[C:9]1([C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:7][CH2:6][CH2:5][C:1]#[N:2])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 962WaterHCID 8929Sodium CyanideHCID 104017744,4-Diphenyl-3-butenyl bromide

生成物 1

HCID 123566855,5-Diphenylpent-4-enenitrile収率 80%

試薬・触媒・溶媒 1

HCID 12679Hexamethylphosphoramide溶媒2 回

実験手順

To a stirred solution of 73.g (1.5 mol) of sodium cyanide in 1 liter of hexamethylphosphoramide at ambient temperature was added over a 1 hour period a solution of 290. g (1 mol) of 4-bromo-1,1-diphenyl-1-butene in 0.5 liters of hexamethylphosphoramide. The mixture was stirred overnight, poured into 2 liters of water and extracted with 3×1 liters of ether. The ether extracts were combined, washed with 3×0.5 liters of Water, 0.5 liters of brine, and dried over sodium sulfate. The resulting crude solid was recrystallized from isopropyl ether to give 190 .g (80%) of 5,5-diphenyl-4-pentenenitrile as a white solid (mp 64°-66° C.) .

後処理

  1. extractionextracted with 3×1 liters of ether
  2. washwashed with 3×0.5 liters of Water, 0.5 liters of brine
  3. dry with materialdried over sodium sulfate
  4. customThe resulting crude solid was recrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-0eb4031750db44dd85485c3bbc3bc705
出典データセット
uspto-grants-1994_08
特許番号
US05334720

反応ノート

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