Dimethyl Sulfide → 2-Methyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 1951532Notes

Reaction equation

HRID 1951532 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2/[CH:13]=C/C.[O:16]=[O+][O-].CSC>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[O:16]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 574388872-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

Product 1

HCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

18.5 g (62.8 mmol) of 2-methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one are dissolved in 400 ml of dichloromethane and cooled to −60° C. Ozone is passed into the reaction solution for 30 min. Dimethyl sulfide is then added to the reaction mixture. After warming to room temperature, the solvent is removed in vacuo, and the residue is slurried in a little methanol. The solid remaining after filtration is recrystallized from diethyl ether. 9.1 g (77.4% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter warming to room temperature
  2. customthe solvent is removed in vacuo
  3. filtrationafter filtration
  4. customis recrystallized from diethyl ether

Sources & evidence

ORD record
ord-7fc519493a7b48ee858f2f04bca45527
Source dataset
uspto-grants-2013_03
Patent number
US08404723B2

Reaction notes

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