Methyl iodide → HCID 22995024, compound

HRID 1168042Notes

Reaction equation

HRID 1168042 reaction equation
[Br:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[C:6]3([CH3:15])[CH2:13][CH2:12][C:9]([CH3:14])([C:10]=2[CH:11]=1)[CH2:8][CH2:7]3.[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[C:6]3([CH3:15])[CH2:13][CH2:12][C:9]([CH3:14])([CH2:8][CH2:7]3)[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22995025HCID 22995025, compound2×

Product 1

HCID 22995024HCID 22995024, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-bromo-1,8-dimethyl-tricyclo[6.2.2.02,7]dodeca-2(7),3,5-trien-4-ol (Compound 3, 0.825 g, 2.94 mmol) in 10 mL of anhydrous acetone was added potassium carbonate (0.128 g, 8.82 mmol) and iodomethane (0.1 mL, 8.82 mmol). The reaction mixture was stirred at 25° C. for 12 hours and filtered. The filtrate was concentrated, and then it was diluted with ether and washed with water and brine. The organic layer was dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate:hexane (5:95) to yield the title compound as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. additionit was diluted with ether
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-70bdb253e41b439a89daa16f987d37ab
Source dataset
uspto-grants-2003_09
Patent number
US06620963B1

Reaction notes

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