Diiodomethane → 4-(1-Methylcyclopropyl)cyclohexanone

HRID 1419808노트

반응식

HRID 1419808 반응식
[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

참가 물질

6

반응물 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 5492914-(1-Methylethenyl)cyclohexanoneHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 541016014-(1-Methylcyclopropyl)cyclohexanone

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
-60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1527b35168534654a5c8f8b41ab5f3a1
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05889012

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