1-Bromopentane → 2-Phenylheptanenitrile

HRID 540381ノート

反応式

HRID 540381 の反応式
[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

参加物

5

反応物 3

HCID 80571-BromopentaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

生成物 1

HCID 126520202-Phenylheptanenitrile収率 64%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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%.

後処理

  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%

出典と根拠

ORDレコード
ord-d8c9f7c69aa44e8db8cfdbd2105b8638
出典データセット
uspto-grants-2014_10
特許番号
US08871187B2

反応ノート

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