Water → Benzonitrile, 4-(4-pentenyl)-

HRID 2254987ノート

反応式

HRID 2254987 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH:12]=O)=[CH:5][CH:4]=1)#[N:2].O.[CH3:15]OC(C)(C)C>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH2:10][CH2:11][CH:12]=[CH2:15]

参加物

5

反応物 3

HCID 962WaterHCID 15413tert-Butyl methyl ether2 回HCID 19739392HCID 19739392、化合物

生成物 1

HCID 11147987Benzonitrile, 4-(4-pentenyl)-

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

実験手順

A suspension of 6.5 g of methyl-triphenylphosphonium bromide in 50 ml of t-butyl methyl ether was treated with 2.1 g of potassium t-butylate at -5° C. and the mixture was then stirred at room temperature for 40 minutes. Subsequently, the mixture was treated at 0° C. with a solution of 2.6 g of 4-(p-cyanophenyl)butyraldehyde in 30 ml of t-butyl methyl ether and the resulting mixture was stirred for 1 hour at room temperature. Thereafter, the reaction mixture was treated with water and extracted three times with diethyl ether. The organic phases were washed twice with water, dried over magnesium sulphate, filtered and concentrated. The crystalline residue was dissolved in hot ethyl acetate, the solution was treated with petroleum ether and the precipitated triphenylphosphine was filtered off. The oil obtained after concentrating the filtrate was purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 5:95), whereby 1.92 g of p-(4-pentenyl)benzonitrile were isolated as a light yellowish liquid.

後処理

  1. stirringthe resulting mixture was stirred for 1 hour at room temperature
  2. extractionextracted three times with diethyl ether
  3. washThe organic phases were washed twice with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crystalline residue was dissolved in hot ethyl acetate
  8. additionthe solution was treated with petroleum ether
  9. filtrationthe precipitated triphenylphosphine was filtered off
  10. customThe oil obtained
  11. concentrationafter concentrating the filtrate
  12. customwas purified by chromatography on silica gel with ethyl acetate/petroleum ether (vol. 5:95)

出典と根拠

ORDレコード
ord-50e7604eca9e466dbc974483f3420397
出典データセット
uspto-grants-1993_08
特許番号
US05238602

反応ノート

読み込み中…