Water → HCID 21276494, compound

HRID 1381686Notes

Reaction equation

HRID 1381686 reaction equation
[C:1]([CH:5]1[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2].[CH3:12][O:13][CH2:14][CH2:15]Br.O>CS(C)=O>[C:1]([C:5]1([CH2:15][CH2:14][O:13][CH3:12])[C:10](=[O:11])[CH2:9][CH2:8][S:7][CH2:6]1)([O:3][CH3:4])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 809722-Bromoethyl methyl etherHCID 10374916Methyl 4-oxothiane-3-carboxylate

Product 1

HCID 21276494HCID 21276494, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5.3 g (25 mmol) of potassium enolate of 4H-2,3,5,6-tetrahydro-3-carbomethoxythiopyran-4-one in 50 ml DMSO, was added 3.47 g (25 mmol) of 2-bromoethyl methyl ether. The solution was stirred under N2 at room temperature for 4 days. The reaction mixture was poured into 500 ml H2O and extracted three times with ethyl acetate. The combined ethyl acetate solution was washed with water; 5% NaOH; H2O and brine; dried over magnesium sulfate, filtered and concentrated in vacuo to give about 5 g crude product. Chromatographed through a pressure column eluting with 10% ethyl acetate-n-hexane to give 2.49 g of the title compound.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give about 5 g crude product
  7. customChromatographed through a pressure column
  8. washeluting with 10% ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-97c781a689a743eea027e1402c36d744
Source dataset
uspto-grants-1989_02
Patent number
US04803286

Reaction notes

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