Dimethyl Sulfide → HCID 21476898, compound

HRID 2293581Notes

Reaction equation

HRID 2293581 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH:14]=C)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3].[O:16]=[O+][O-].CSC>CO.C(Cl)Cl>[CH:14]([C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3])=[O:16]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone3×HCID 21476907HCID 21476907, compound

Product 1

HCID 21476898HCID 21476898, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of 2.796 g (14.0 mmol) of the product of Step B dissolved in a mixture of 15 mL methanol and 5 mL methylene chloride was introduced a slow stream of ozone at -78° C. After 15 minutes a persistent blue color of excess ozone was observed and the flow of ozone was stopped. Excess methylsulfide (2 mL) was added via syringe, the reaction mixture was allowed to warm to room temperature, and stirring was continued for 12 hours. The reaction mixture was then concentrated on a rotary evaporator and then purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 1.677 g (59%) of the title compound as a clear oil.

Workup

  1. concentrationThe reaction mixture was then concentrated on a rotary evaporator
  2. custompurified on a silica gel flash chromatography column
  3. washeluted with 5% EtOAc-hexane
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-84124b06bf244c98a82125e7aaa1eae5
Source dataset
uspto-grants-1997_11
Patent number
US05686478

Reaction notes

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