Pyridine → 3-Methyl-1-phenylsulfanyl-butan-2-one

HRID 2405876Notes

Reaction equation

HRID 2405876 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Br[CH2:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18]>C(OCC)C.CCOC(C)=O>[CH3:18][CH:17]([CH3:19])[C:16](=[O:20])[CH2:15][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7969ThiophenolHCID 108990371-Bromo-3-methylbutan-2-one

Product 1

HCID 5512653-Methyl-1-phenylsulfanyl-butan-2-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of thiophenol (4.44 mL; 43.4 mmol) in diethyl ether (29 mL) was added pyridine (17.2 mL; 0.21 mol), followed by the drop-wise addition of a solution of compound 563-B (7.18 g; 43.5 mmol) in diethyl ether (15 mL), at ambient temperature, and the reaction was stirred for 72 h. The reaction was diluted with EtOAc, washed with 2N HCl, H2O, brine, dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude residue was purified by flash column chromatography (SiO2) eluting with a heptane-EtOAc gradient to afford compound 563-C as an oil. 1H-NMR (CDCl3): δ 1.09-1.10 (d, 6H), 2.90-2.97 (m, 1H), 3.75 (s, 2H), 7.18-7.35 (m, 5H).

Workup

  1. washwashed with 2N HCl, H2O, brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe crude residue was purified by flash column chromatography (SiO2)
  6. washeluting with a heptane-EtOAc gradient

Sources & evidence

ORD record
ord-ad84b976f54d40fc8128ab3d00c607b3
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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