Diiodomethane → 4-(1-Methylcyclopropyl)cyclohexanone

HRID 1419808ノート

反応式

HRID 1419808 の反応式
[C:1]([CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)([CH3:3])=[CH2:2].[CH2:11]([Zn]CC)C.ICI.[NH4+].[Cl-]>CCCCCC>[CH3:2][C:1]1([CH:4]2[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[CH2:11][CH2:3]1

参加物

6

反応物 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 5492914-(1-Methylethenyl)cyclohexanoneHCID 178418750HCID 178418750、化合物

生成物 1

HCID 541016014-(1-Methylcyclopropyl)cyclohexanone

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
-60 °C

実験手順

5.0 g (0.036 mol) of 4-isopropenylcyclohexanone (precursor to Example 4) were placed under inert gas in 150 ml of hexane, and 16.5 g (0.134 mol) of diethylzinc (1M in hexane) followed by 58.0 g (0.22 mol) of diiodomethane were added dropwise at -20° C. The mixture was stirred at -60° C. for 2 hours and then at 0° C. for 6 hours. The reaction solution was kept in a refrigerator overnight and was worked up by pouring it into cold NH4Cl solution and carrying out extraction with ether. The organic phase was washed with sodium thiosulfate solution and water, dried and concentrated. 5.3 g (96% of theory) of a colorless oil were obtained which was reacted without further purification.

後処理

  1. additionwere added dropwise at -20° C
  2. waitat 0° C. for 6 hours
  3. customwas kept in a refrigerator overnight
  4. extractionextraction with ether
  5. washThe organic phase was washed with sodium thiosulfate solution and water
  6. customdried
  7. concentrationconcentrated
  8. custom5.3 g (96% of theory) of a colorless oil were obtained which
  9. customwas reacted without further purification

出典と根拠

ORDレコード
ord-1527b35168534654a5c8f8b41ab5f3a1
出典データセット
uspto-grants-1999_03
特許番号
US05889012

反応ノート

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