Acetonitrile → (+/-)-Ethanethioic acid S-[5-(2,4-difluorophenyl)tetrahydro-3-furanyl]ester

HRID 1450322Notes

Reaction equation

HRID 1450322 reaction equation
Br[CH:2]1[CH2:6][O:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=2[F:14])[CH2:3]1.[C:15]([O-:18])(=[S:17])[CH3:16].[K+].C(#N)C>C(OCC)(=O)C.CCCCCC>[F:14][C:8]1[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=1[CH:4]1[O:5][CH2:6][CH:2]([S:17][C:15](=[O:18])[CH3:16])[CH2:3]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23670855Potassium ethanethioateHCID 85719042(+/-)-4-Bromo-2-(2,4-difluorophenyl)tetrahydrofuran

Product 1

HCID 85719043(+/-)-Ethanethioic acid S-[5-(2,4-difluorophenyl)tetrahydro-3-furanyl]esterYield 76.7%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound is prepared by the procedure of Example 5 using 1.9 g of product from Example 165, 0.866 g of potassium thioacetate and 30 ml of acetonitrile to give, after chromatography (silica gel: 5% ethyl acetate/hexane), 1.43 g of the desired product, as a mixture of isomers.

Workup

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Sources & evidence

ORD record
ord-2ae2863773264413bebbabf4ddb90eb4
Source dataset
uspto-grants-1997_02
Patent number
US05602118

Reaction notes

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