2-(2-(Methacryloyloxy)ethylthio)acetic acid → 2-(2-(Methacryloyloxy)ethylsulfinyl)acetic acid

HRID 523619Notes

Reaction equation

HRID 523619 reaction equation
[C:1]([O:6][CH2:7][CH2:8][S:9][CH2:10][C:11]([OH:13])=[O:12])(=[O:5])[C:2]([CH3:4])=[CH2:3].I([O-])(=O)(=O)=[O:15].[Na+].C(Cl)(Cl)Cl.CO.C(O)(C(F)(F)F)=O>C(#N)C.O>[C:1]([O:6][CH2:7][CH2:8][S:9]([CH2:10][C:11]([OH:13])=[O:12])=[O:15])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

6

Reactant 3

HCID 149584532-(2-(Methacryloyloxy)ethylthio)acetic acidHCID 22462991CHCl3 MeOH TFAHCID 23667635Sodium periodate

Product 1

HCID 871700522-(2-(Methacryloyloxy)ethylsulfinyl)acetic acidYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4 (1 g, 4.9 mmol, 1 eqv.) in acetonitrile (ACN) (10 mL) was mixed with a sodium periodate solution (1.1 g, 4.9 mmol, 1 eqv.) dissolved in H2O (10 mL). The reaction mixture was stirred at RT overnight. The completion of the reaction was confirmed by TLC(CHCl3/MeOH/TFA, 75:25:0.1 (v/v), Rf: 0.23). The reaction mixture was filtered via suction filtration to remove sodium iodate salts by EtOAc and dried with MgSO4 and filtered through Ø 185 mm whatman filter papers. The filtrate was concentrated in vacuo and co-evaporated with CH2Cl2. 0.87 g (81% yield) 5 was obtained as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered via suction filtration
  2. customto remove sodium iodate salts by EtOAc
  3. dry with materialdried with MgSO4
  4. filtrationfiltered through Ø 185 mm whatman
  5. filtrationfilter papers
  6. concentrationThe filtrate was concentrated in vacuo and co-evaporated with CH2Cl2

Sources & evidence

ORD record
ord-85ae980117e241098f91fffde810a178
Source dataset
uspto-grants-2016_05
Patent number
US09339554B2

Reaction notes

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