Thiophenol → 4-phenylsulfanyl-[1,3]dioxolan-2-one

HRID 1822616Notes

Reaction equation

HRID 1822616 reaction equation
[C:1]1(=[O:6])[O:5][CH:4]=[CH:3][O:2]1.[C:7]1([SH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>O1CCCC1>[C:7]1([S:13][CH:3]2[CH2:4][O:5][C:1](=[O:6])[O:2]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 13385Vinylene carbonate

Product 1

HCID 112870574-phenylsulfanyl-[1,3]dioxolan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 70 mL of tetrahydrofuran (THF), 3 g of vinylene carbonate and 5.1 g of benzenethiol were dissolved, and then 4.7 g of triethylamine was added. The mixture was refluxed under an argon atmosphere for 4 hours. When the reaction was finished, the solvent was removed through distillation under reduced pressure, and the resulting material was subjected to the column chromatography on silica gel (eluted with 20% hexane/ethylacetate) and purified to obtain a target product, 4-phenylsulfanyl-[1,3]dioxolan-2-one.

Workup

  1. temperatureThe mixture was refluxed under an argon atmosphere for 4 hours
  2. customthe solvent was removed through distillation under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-0756cdc0e6a8450e9993aa36a63b75ac
Source dataset
uspto-grants-2006_05
Patent number
US07037624B2

Reaction notes

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