Potassium Carbonate → (S)-Methyl 3-((2-methoxyphenyl)thio)-2-methylpropanoate

HRID 601732Notes

Reaction equation

HRID 601732 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].[CH3:16][C@H:17]([CH2:22]OS(C)(=O)=O)[C:18]([O:20][CH3:21])=[O:19]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][CH2:16][C@@H:17]([CH3:22])[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23642ThioguaiacolHCID 86621909methyl (2R)-2-methyl-3-[(methylsulfonyl)oxy]propanoate

Product 1

HCID 59809200(S)-Methyl 3-((2-methoxyphenyl)thio)-2-methylpropanoate

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a round-bottom flask maintained under an inert atmosphere, 4.72 mL (38.8 mmoles) of 2-methoxythiophenol, 10.72 g (77.6 mmoles) of potassium carbonate, 5.13 g of diluted methyl (2R)-2-methyl-3-[(methylsulfonyl)oxy]propanoate (6a-1) and 100 mL of anhydrous THF then 329 mg (0.97 mmole) of tetrabutylammonium hydrogen sulfate are introduced. The reaction medium is brought to 60° C. for 24 h under vigorous stirring then concentrated under reduced pressure. The residue is taken up with water and is extracted with ethylic ether. The combined organic phases are washed with a 1 N soda solution, water, brine, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is taken up in methanol and concentrated then taken up again in methanol (10 mL/1 g of residue). The bis(methoxyphenyl) disulfide [13920-94-0] that slowly precipitates is eliminated by filtration. The filtrate is evaporated under reduced pressure to yield the title compound in the form of a pale yellow oil (6.4 g, 26.6 mmoles).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. extractionis extracted with ethylic ether
  3. washThe combined organic phases are washed with a 1 N soda solution, water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. concentrationconcentrated
  8. customThe bis(methoxyphenyl) disulfide [13920-94-0] that slowly precipitates
  9. filtrationis eliminated by filtration
  10. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-fa5ef9b50f224b4188d19940301f6d7b
Source dataset
uspto-grants-2011_03
Patent number
US07902381B2

Reaction notes

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