Water → HCID 54213073, compound

HRID 1871652Notes

Reaction equation

HRID 1871652 reaction equation
CO[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12](OS(C)(=O)=O)[C:13](OCC)=O)=[CH:7][CH:6]=1.[CH3:23][S-:24].[Na+].[C:26](OCC)(=[O:28])[CH3:27].[OH2:32].[CH3:33]N(C)C=O>>[CH3:33][O:32][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH3:13])[C:23]([O:28][CH2:26][CH3:27])=[S:24])=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 18692615HCID 18692615, compound

Product 1

HCID 54213073HCID 54213073, compound

Procedure

A solution of 17.2 g of ethyl 3-(4-methoxymethoxyphenyl)-2-methanesulfonyloxypropionate, 4.20 g of sodium thiomethoxide in 300 ml of N,N-dimethylformamide was stirred at 50° C. for 1.5 hours. After the reaction, ethyl acetate and water were added to the reaction mixture. Then, the ethyl acetate layer was separated and dried over anhydrous magnesium sulfate. The extract thus obtained was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 11.37 g of the desired compound as a syrup.

Workup

  1. additionwere added to the reaction mixture
  2. customThen, the ethyl acetate layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. extractionThe extract thus
  5. customobtained
  6. concentrationwas concentrated

Sources & evidence

ORD record
ord-95c00179aecc4ea394f5bfb1f67298f2
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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