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

HRID 1048107Notes

Reaction equation

HRID 1048107 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-08d4ff93013b456fb18cf4e94e38d4cf
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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