Methyl iodide → (3,5-Dimethoxyphenyl)-(2,3,4-trimethoxyphenyl)methanone

HRID 970973Notes

Reaction equation

HRID 970973 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=2[OH:23])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.IC.[C:26]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=2[O:23][CH3:26])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 69205198(3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone

Product 1

HCID 69203226(3,5-Dimethoxyphenyl)-(2,3,4-trimethoxyphenyl)methanoneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

To a mixture of (3,5-dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl) methanone (1.59 g, 5.00 mmol) in DMF (25 ml) was added iodomethane (0.62 ml, 10.00 mmol), and powdered Na2CO3 (1.06 g, 10.00 mmol) at rt. The suspension was stirred at ˜35° C. overnight. DMF was evaporated in vacuo and to the residue was added CH2Cl2 (100 ml) and washed with H2O (3×80 ml). The white salt was filtered and the solution was washed with 5 N KOH (4×80 ml), H2O (1×80 ml), dried over MgSO4 and concentrated to a brown oil, which was purified via flash column chromatography (20% EtOAc in hexane) to give (3,5-dimethoxy-phenyl)-(2,3,4-trimethoxy-phenyl)methanone as a clear oil (1.49 g, 90%): 1HNMR (CDCl3) δ 7.12 (d, J=8 Hz, 1H, Ar), 6.94 (d, J=2 Hz, 2H, Ar), 6.71 (d, J=8 Hz, 1H, Ar), 6.65 (t, J=2 Hz, 1H, Ar), 3.93 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 3.81 (s, 6H, 2OCH3), 3.79 (s, 3H, OCH3); 13C NMR (CDCl3) δ 195.2, 160.7, 156.3, 152.9, 142.2, 140.5, 126.6, 125.1, 107.7, 106.8, 105.4, 62.0, 61.1, 56.3, 55.7; Anal. Calcd. For C18H20O6: C, 65.05; H, 6.07. Found: C, 64.93; H, 6.09. The product was carried over to the next step.

Workup

  1. customDMF was evaporated in vacuo and to the residue
  2. additionwas added CH2Cl2 (100 ml)
  3. washwashed with H2O (3×80 ml)
  4. filtrationThe white salt was filtered
  5. washthe solution was washed with 5 N KOH (4×80 ml), H2O (1×80 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a brown oil, which
  8. customwas purified via flash column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-c14554608a2140ab807ea29ab23d8932
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

Loading…