Methyl iodide → HCID 57682877, compound

HRID 495008Notes

Reaction equation

HRID 495008 reaction equation
[OH:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:15])=[CH:4][CH:3]=1.IC.[C:18](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:18][O:1][C:2]1[C:11]([CH2:12][CH:13]=[CH2:14])=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57682834HCID 57682834, compound

Product 1

HCID 57682877HCID 57682877, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

160 mg of 3,4-dihydro-7-hydroxy-8-(2-propenyl)-1(2H)-naphthalenone (CAS No. 122076-30-6), 140 mg of iodomethane, and 400 mg of potassium carbonate were dissolved in 15 ml of acetone. The reaction solution was then stirred at 70° C. for 1.5 hours. The mixture was filtered and then washed with acetone. The organic layer was then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography, so that 140 mg of the subject compound was obtained from an ethyl acetate-hexane eluate (1:10).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with acetone
  3. concentrationThe organic layer was then concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography, so that 140 mg of the subject compound
  5. customwas obtained from an ethyl acetate-hexane eluate (1:10)

Sources & evidence

ORD record
ord-5b15b53ec05540d88ff1807cc315c5fe
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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