Methyl iodide → HCID 77230947, compound

HRID 1056908Notes

Reaction equation

HRID 1056908 reaction equation
[OH:1][C:2]1[C:3](=[O:14])[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1.I[CH3:16]>CC(C)=O>[CH3:16][O:1][C:2]1[C:3](=[O:14])[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 77230946HCID 77230946, compound

Product 1

HCID 77230947HCID 77230947, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of crude 5-hydroxy-2-phenyl-4H-pyran-4-one (0.4 mmol) in acetone (10.9 mL) is added iodomethane (0.7 mL, 1 1.3 mmol) and the reaction mixture was heated at 60° C. for 2 h. After being cooled to room temperature, the reaction was concentrated under reduced pressure and diluted with CHCl3 (10 mL) and water (10 mL). The layers were separated and the organic fraction washed with sat. aq. NaCl, dried (Na2SO4), and concentrated under reduced pressure to provide (93%) of 5-methoxy-2-phenyl-4H-pyran-4-one as tan crystals which were used in the subsequent step without further purification. LC/MS (M+H)+ 203.

Workup

  1. temperatureAfter being cooled to room temperature
  2. concentrationthe reaction was concentrated under reduced pressure
  3. additiondiluted with CHCl3 (10 mL) and water (10 mL)
  4. customThe layers were separated
  5. washthe organic fraction washed with sat. aq. NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bfa7b0d855245a989b636b66995a1af
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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