m-Chloroperbenzoic acid → HCID 58381702, compound

HRID 410049Notes

Reaction equation

HRID 410049 reaction equation
[CH2:1]([S:16][CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=[O:19])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15].C1C=C(Cl)C=C(C(OO)=[O:31])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:16]([CH:17]([CH2:21][CH3:22])[C:18]([OH:20])=[O:19])=[O:31])[CH2:2]/[CH:3]=[CH:4]\[CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58381686HCID 58381686, compound

Product 1

HCID 58381702HCID 58381702, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-20 °C

Procedure

2-((3Z,6Z,9Z,12Z)-Pentadeca-3,6,9,12-tetraenylthio)butanoic acid (0.20 g, 0.62 mmol) was dissolved in dry CHCl3 (10 mL) and the solution was cooled down to −20° C. under inert atmosphere. mCPBA (˜77%, 0.15 g, 0.68 mmol) dissolved in dry CHCl3 (2 mL) was added dropwise and the resulting solution was stirred at −20° C. for 35 minutes. The solvents were evaporated in vacuo, the residue was added heptane (10 mL) and the resulting white precipitate was removed by filtration. The filtrate was concentrated in vacuo and the residue was added heptane (10 mL). The resulting white precipitate was again removed by filtration. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (heptane:EtOAc+w/1% HCOOH 4:1-1:1). Concentration of the appropriate fractions afforded 100 mg (48% yield) of the title compound as an oil.

Workup

  1. additionwas added dropwise
  2. customThe solvents were evaporated in vacuo
  3. additionthe residue was added heptane (10 mL)
  4. customthe resulting white precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionthe residue was added heptane (10 mL)
  7. customThe resulting white precipitate was again removed by filtration
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by flash chromatography on silica gel (heptane:EtOAc+w/1% HCOOH 4:1-1:1)

Sources & evidence

ORD record
ord-c9f9d8f397c94bc1b1347a16da06fe91
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

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