3-Mercaptopropionic Acid → HCID 178526190, compound

HRID 2285865Notes

Reaction equation

HRID 2285865 reaction equation
S[CH2:2][CH2:3][C:4]([OH:6])=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])([CH2:2][CH2:3][C:4]([OH:6])=[S:24])[C:32]([F:35])([F:34])[F:33]

Participants

5

Procedure

2.0 ml of methylene chloride, 0.05 ml (0.58 mmol) of 3-mercaptopropionic acid and 120 mg (0.59 mmol) of 2,6-di-tert-butyl-4-methylpyridine were charged in a flask, and 261 mg (0.55 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 white precipitate was filtered, subjected to column chromatography of a small amount of silica gel and, after eluting iodobenzene with hexane, the desired product was eluted with diethyl ether. Diethyl ether was distilled off from the eluate to obtain 3-pentafluoroethylthiopropionic acid as a colorless liquid. A sample of the product was purified by gas chromatography. Yield, 83%.

Workup

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

Sources & evidence

ORD record
ord-650e86ea3f6541ceb19cc261655d8eaf
Source dataset
uspto-grants-1982_04
Patent number
US04324741

Reaction notes

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