1-Bromopentane → 2-Phenylheptanenitrile

HRID 540381노트

반응식

HRID 540381 반응식
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>CN(C=O)C>[C:1]1([CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 80571-BromopentaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

생성물 1

HCID 126520202-Phenylheptanenitrile수율 64%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

5 g (42.7 mmol) of phenylacetonitrile are added dropwise to a suspension of 2 g of 60% NaH in 50 ml of DMF cooled to 0° C. After stirring for 30 minutes at 0° C., 5.32 ml (42.7 mmol) of bromopentane are added dropwise. The reaction medium is stirred for 16 hours at ambient temperature and then treated with ice and extracted with ethyl ether. The organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over sodium sulphate, filtered and evaporated under pressure. An orangey-yellow oil is obtained and purified by fractionated distillation under reduced pressure (70-75° C. under 1×10−1 mbar). 5.14 g in the form of an orangey oil are obtained with a yield of 64%.

후처리

  1. stirringThe reaction medium is stirred for 16 hours at ambient temperature
  2. additiontreated with ice
  3. extractionextracted with ethyl ether
  4. washThe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated under pressure
  8. customAn orangey-yellow oil is obtained
  9. distillationpurified by fractionated distillation under reduced pressure (70-75° C. under 1×10−1 mbar)
  10. custom5.14 g in the form of an orangey oil are obtained with a yield of 64%

출처 및 근거

ORD 기록
ord-d8c9f7c69aa44e8db8cfdbd2105b8638
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871187B2

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