Dimethyl Sulfide → HCID 86656221, compound

HRID 451569Notes

Reaction equation

HRID 451569 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:11][CH2:12][CH:13]=C)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[O:16]=[O+][O-].CSC>ClCCl>[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:11][CH2:12][CH:13]=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 13341026HCID 13341026, compound

Product 1

HCID 86656221HCID 86656221, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-75 °C

Procedure

Allyloxy-phenyl-acetic acid methyl ester (described in EJOC 2000, 3145-3163; 3 g, 14.5 mmol) was dissolved in dichloromethane (300 mL) and cooled to −75° C. O3 was blubbled through the solution for 6 hours until the solution turned blue. Argon was blubbled through the solution for 1 hour, then dimethyl sulfide (9.04 g, 10.8 mL, 145 mmol) was added to the reaction mixture and kept at room temperature for 12 hours. The reaction mixture was evaporated and the residue purified by flash chromatography over 50 g SiO2-flash pack using gradient 10-100% EtOAc in heptane over 60 minutes to give the title compound as light yellow oil (2.72 g, 90%).

Workup

  1. waitkept at room temperature for 12 hours
  2. customThe reaction mixture was evaporated
  3. customthe residue purified by flash chromatography over 50 g SiO2-flash pack
  4. customover 60 minutes

Sources & evidence

ORD record
ord-6edfb91844584cdcad8795f13b83da73
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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