Diiodomethane → 4-(1-Methylcyclopropyl)cyclohexanone

HRID 1419808Notes

Reaction equation

HRID 1419808 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 541016014-(1-Methylcyclopropyl)cyclohexanone

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-60 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1527b35168534654a5c8f8b41ab5f3a1
Source dataset
uspto-grants-1999_03
Patent number
US05889012

Reaction notes

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