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

HRID 557390Notes

Reaction equation

HRID 557390 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-5dc37c69728d495e9667d0815d48ea58
Source dataset
uspto-grants-2011_11
Patent number
US08058447B2

Reaction notes

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