Methyl iodide → HCID 72943024, compound

HRID 1854675Notes

Reaction equation

HRID 1854675 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1.[H-].[Na+].[CH3:16]I>CN(C)C=O.C(OCC)(=O)C.[NH4+].[Cl-]>[CH3:16][O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[O:5][C:4](=[O:13])[CH:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 546863494-Hydroxy-6-methyl-2H-1-benzopyran-2-one

Product 1

HCID 72943024HCID 72943024, compoundYield 43.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 4-hydroxy-6-methylcoumarin (300 mg, 1.70 mmol) in 3.4 mL of dry N,N-dimethylformamide was added sodium hydride (89 mg, 55%, 2.0 mmol) under nitrogen at 0° C. After the reaction mixture was stirred at room temperature for 30 min, methyl iodide (0.16 mL, 2.6 mmol) was added with additional stirring for 30 min. The reaction mixture was diluted with 10 mL of ethyl acetate and 10 mL of saturated NH4Cl aqueous solution at 0° C., successively, and the solution was extracted with 100 mL of ethyl acetate. The extract was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the solution was concentrated in vacuo to obtain crude 4-methoxy-6-methylcoumarin (140 mg, 43%).

Workup

  1. stirringwith additional stirring for 30 min
  2. extractionsuccessively, and the solution was extracted with 100 mL of ethyl acetate
  3. washThe extract was washed with saturated NaHCO3 aqueous solution, brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4cb0b21e58ef44d196ba86d8917ed82c
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

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