Dimethyl Sulfide → HCID 14572861, compound

HRID 218227Notes

Reaction equation

HRID 218227 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH2:10][CH:11]=C)([CH3:9])[C:5]([O:7][CH3:8])=[O:6].CSC.C(Cl)Cl.C[OH:21]>>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:9])([CH2:10][CH:11]=[O:21])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 18730405HCID 18730405, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 14572861HCID 14572861, compound

Conditions

Temperature
-78 °C

Procedure

A solution of the product of Example 31A (1.1 gm, 5.9 mmol) was dissolved in CH2Cl2/MeOH 10:1 (15 mL) and cooled to −78° C. To the solution was bubbled O3 over 20 minutes. The reaction solution was purged with N2 for a further 10 minutes and dimethyl sulfide (DMS) (3.6 gm, 59 mmol) was added and the reaction warmed to ambient temperature and stirred for a further 2 hours. The solvent was evaporated in vacuo and product purified by flash column chromatography (hexane/EtOAc 100:0 to 70:30) to collect Example 31B as an oil.

Workup

  1. customTo the solution was bubbled O3 over 20 minutes
  2. customThe reaction solution was purged with N2 for a further 10 minutes
  3. temperaturethe reaction warmed to ambient temperature
  4. customThe solvent was evaporated in vacuo and product
  5. custompurified by flash column chromatography (hexane/EtOAc 100:0 to 70:30)
  6. customto collect Example 31B as an oil

Sources & evidence

ORD record
ord-40bb42b6a2934436881b4f1cbd4305fb
Source dataset
uspto-grants-2012_06
Patent number
US08198331B2

Reaction notes

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