Methyl iodide → HCID 86749153, compound

HRID 2259999Notes

Reaction equation

HRID 2259999 reaction equation
[CH3:1][C:2]1[C:3](/[C:16](/[CH3:28])=[CH:17]/[C:18]2[NH:19][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.CI.[C:31]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[C:3](/[C:16](/[CH3:28])=[CH:17]/[C:18]2[N:19]([CH3:31])[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:22]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15341373HCID 15341373, compound2×

Product 1

HCID 86749153HCID 86749153, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl (E)-2-[2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethylnaphthalen-2-yl)propen-1-yl]-5-imidazolecarboxylate (Compound 5, 25 mg, 0.066 mmol) was dissolved in acetone (3 mL) at room temperature and treated with methyl iodide (0.025 mL) and K2CO3 (100 mg). The suspension was stirred for 24 hours, filtered through Celite and concentrated under reduced pressure. The residue was treated with water (5 mL) and the organic material was extracted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=5:1) to give the title compound as a light yellow solid (14 mg, 54%).

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with water (5 mL)
  4. extractionthe organic material was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (hexanes/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-eaff561ba9be47719bb0d7cb4b5ecf46
Source dataset
uspto-grants-1995_12
Patent number
US05475113

Reaction notes

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