HCID 15351908, compound → HCID 86634461, compound

HRID 546336Notes

Reaction equation

HRID 546336 reaction equation
FC(F)(F)S(O[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][C:8]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=O)=O.[C:24]([O-:27])(=[S:26])[CH3:25].[K+]>CN(C)C=O>[C:24]([S:26][C:7]1[CH2:16][CH2:15][C:10]2([O:11][CH2:12][CH2:13][O:14]2)[CH2:9][C:8]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:27])[CH3:25]

Participants

4

Reactant 2

HCID 15351908HCID 15351908, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 86634461HCID 86634461, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

19.97 g (55.4 mmol) of ethyl 8-trifluoromethanesulfonyloxy-1,4-dioxaspiro[4.5]dec-7-ene-7-carboxylate [compound described as compound 6 in Tetrahedron Letter, Vol. 39, pp. 6139-6142 (1998)] was dissolved in 200 ml of dimethylformamide, and 9.50 g (83.1 mmol) of potassium thioacetate was added thereto with stirring under ice-cooling, followed by stirring at room temperature for 91 hours. To the reaction solution was added ice water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel column chromatography (solvent; hexane:ethyl acetate=17:3) to give 7.15 g of the title compound as a pale brown oil (yield: 45%).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 91 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-5f05c6718b01407c98a2df7dc401981d
Source dataset
uspto-grants-2011_05
Patent number
US07935835B2

Reaction notes

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