HCID 15351908, compound → HCID 86634461, compound

HRID 2191148Notes

Reaction equation

HRID 2191148 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-92176d2322b346d49a1960cc842d7e3e
Source dataset
uspto-grants-2012_12
Patent number
USRE043858E1

Reaction notes

Loading…