(+-)-2-Mercaptopropionic acid → HCID 178460598, compound

HRID 1758182Notes

Reaction equation

HRID 1758182 reaction equation
S[CH:2]([CH3:6])[C:3]([OH:5])=O.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)[S:24]([O-])(=O)=O.[F:30][C:31]([I+]C1C=CC=CC=1)([F:36])[C:32]([F:35])([F:34])[F:33]>C(Cl)Cl>[F:30][C:31]([F:36])([CH:2]([CH3:6])[C:3]([OH:5])=[S:24])[C:32]([F:35])([F:34])[F:33]

Participants

5

Reactant 3

HCID 62326(+-)-2-Mercaptopropionic acidHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 11488264Pentafluoroethylphenyliodonium trifluoromethanesulfonate

Product 1

HCID 178460598HCID 178460598, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0 ml of methylene chloride, 0.06 ml (0.68 mmol) of 2-mercaptopropionic acid and 140 mg (0.68 mmol) of 2,6-di-tert-butyl-4-methylpyridine were charged in a flask, and 320 mg (0.68 mmol) of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto in small portions while stirring at room temperature, followed by stirring the mixture at room temperature for 20 minutes. The resulting precipitate was filtered, subjected to column chromatography of silica gel and, after eluting iodobenzene with pentane, the desired product was eluted with diethyl ether. Diethyl ether was distilled off from the eluate to obtain 2-pentafluoroethylthiopropionic acid as a colorless liquid. A sample of the product was purified by gas chromatography. Yield, 81%.

Workup

  1. stirringby stirring the mixture at room temperature for 20 minutes
  2. filtrationThe resulting precipitate was filtered
  3. washafter eluting iodobenzene with pentane
  4. washthe desired product was eluted with diethyl ether
  5. distillationDiethyl ether was distilled off from the eluate

Sources & evidence

ORD record
ord-d523dfa221194dd9aa091bc17712b4df
Source dataset
uspto-grants-1983_02
Patent number
US04371710

Reaction notes

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