Methyl iodide → 7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1021478Notes

Reaction equation

HRID 1021478 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].CI>O1CCCC1>[CH3:13][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 108558177-hydroxy-2,3-dihydro-4H-chromen-4-one

Product 1

HCID 43875107-methoxy-3,4-dihydro-2H-1-benzopyran-4-oneYield 72.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

7-Hydroxy-2,3-dihydrochromen-4-one (4.47 g, 27.2 mmol) was diluted with tetrahydrofuran (40 mL) followed by the addition of K2CO3 (5.64 g, 40.8 mmol) and MeI (2.55 mL, 40.8 mmol). The reaction was heated at 70° C. for 5 hours. The reaction was allowed to cool and loaded onto a Biotage 40M cartridge running a gradient 5% ethyl acetate/hexanes to 75% to yield the title compound (3.5 g, 72.1% yield).

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-92ce8e0785bc455f9f06bd2b5be487d8
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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