Methyl iodide → isoformononetin

HRID 2220822Notes

Reaction equation

HRID 2220822 reaction equation
[CH:1]1[C:6]([C:7]2[C:16](=[O:17])[C:15]3[CH:14]=[CH:13][C:12]([OH:18])=[CH:11][C:10]=3[O:9][CH:8]=2)=[CH:5][CH:4]=[C:3]([OH:19])[CH:2]=1.[C:20]([O-])([O-])=O.[K+].[K+].IC>CS(C)=O>[CH3:20][O:18][C:12]1[CH:11]=[C:10]2[C:15]([C:16](=[O:17])[C:7]([C:6]3[CH:5]=[CH:4][C:3]([OH:19])=[CH:2][CH:1]=3)=[CH:8][O:9]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 5281708Daidzein

Product 1

HCID 3764isoformononetinYield 45.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5.1 g of daidzein (20.06 mmol) in 40 ml of DMSO was added 3.5 g of anhydrous K2CO3 (25.4 mmol) and 6 ml of iodomethane (96.4 mmol). The mixture was stirred at room temperature for 2 hours and then poured into ice water to precipitate product. Precipitates were extracted with ethyl acetate, dried by flash evaporation and purified on a Sephadex LH-20 column (chloroform:methanol/7:3). Final product was recrystallized from acetone to give 2.3 g of crystalline analog 2, a yield of 45.1% (w/w): mp 210-211° C.; 1H NMR (DMSO-d6) δ 3.89 (—OCH3), 6.81 (d, 2H, J=8.43 Hz, 3′, 5′-H), 7.05 (dd, 1H, J=8.89, 2.39 Hz, 6-H), 7.11 (d, 1H, J=2.07 Hz, 8-H), 7.39 (d, 2H, J=8.62 Hz, 2′, 6′-H), 8.01 (d, 1H, J=8.87 Hz; 5-H), 8.35 (s, 1H, 2-H), 9.54 (s, 1H, 4′-OH). Anal. (C16H12O4) for C, H. Cacld: 71.64, 4.51; found: 71.24, 4.47.

Workup

  1. customto precipitate product
  2. customPrecipitates
  3. extractionwere extracted with ethyl acetate
  4. customdried by flash evaporation
  5. custompurified on a Sephadex LH-20 column (chloroform:methanol/7:3)
  6. customFinal product was recrystallized from acetone
  7. customto give 2.3 g of crystalline analog 2

Sources & evidence

ORD record
ord-526dc5d1a9d24bc283e8d36504c33de1
Source dataset
uspto-grants-2008_05
Patent number
US07368434B2

Reaction notes

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