5-Methyl-2-hexanone → 3-Chloro-2-isobutyl-but-2-enal

HRID 1676102ノート

反応式

HRID 1676102 の反応式
P(Cl)(Cl)([Cl:3])=O.[CH3:6][CH:7]([CH3:13])[CH2:8][CH2:9][C:10](=[O:12])C.[CH3:14][C:15]([O-])=O.[Na+]>CN(C=O)C>[Cl:3][C:15]([CH3:14])=[C:9]([CH2:8][CH:7]([CH3:6])[CH3:13])[CH:10]=[O:12]

参加物

5

反応物 3

HCID 80345-Methyl-2-hexanoneHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

生成物 1

HCID 866457643-Chloro-2-isobutyl-but-2-enal収率 125.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
5 °C

実験手順

Phosphorusoxychloride (53.7 g, 350 mmol) is slowly added to DMF (60 mL) stirred at 5° C. Upon complete addition, the clear solution is stirred for further 30 min at 5° C. before 5-methyl-2-hexanone (20 g, 175 mmol) is added dropwise. The yellow solution is stirred for 30 min at 0° C., then for 90 min at rt. The mixture becomes warm (40° C.) and a thick suspension forms. The mixture is cooled to 25° C. and stirring is continued for 1 h before it is poured into an aq. solution of NaOAc (80 g)/ice mixture. The mixture is extracted twice with diethyl ether. The organic extracts are washed with water, combined, dried over MgSO4, filtered and evaporated to give crude 3-chloro-2-isobutyl-but-2-enal (35.4 g) as a yellow oil, LC-MS: tR=0.97 min.

後処理

  1. additionUpon complete addition
  2. additionis added dropwise
  3. stirringThe yellow solution is stirred for 30 min at 0° C.
  4. temperatureThe mixture becomes warm (40° C.)
  5. temperatureThe mixture is cooled to 25° C.
  6. stirringstirring
  7. waitis continued for 1 h before it
  8. extractionThe mixture is extracted twice with diethyl ether
  9. washThe organic extracts are washed with water
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated

出典と根拠

ORDレコード
ord-0c9bccf4b12b414da79762c9ba2603e2
出典データセット
uspto-grants-2011_08
特許番号
US08003800B2

反応ノート

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