Water → Benzonitrile, 4-(4-pentenyl)-

HRID 247690노트

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HRID 247690 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 15413tert-Butyl methyl ether2회HCID 19739392HCID 19739392, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 74505Methyltriphenyliphosphonium bromide촉매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8758539dc32c495daf92ac4999b1804c
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04709030

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