Thioglycolic Acid → HCID 178526196, compound

HRID 1758185Notes

Reaction equation

HRID 1758185 reaction equation
S[CH2:2][C:3]([OH:5])=O.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.FC(F)(F)[S:23]([O-])(=O)=O.[F:29][C:30]([I+]C1C=CC=CC=1)([F:35])[C:31]([F:34])([F:33])[F:32]>C(Cl)Cl>[F:29][C:30]([CH2:2][C:3]([OH:5])=[S:23])([F:35])[C:31]([F:34])([F:33])[F:32]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 11488264Pentafluoroethylphenyliodonium trifluoromethanesulfonate

Product 1

HCID 178526196HCID 178526196, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.12 ml of mercaptoacetic acid and 350 ml of 2,6-di-tert-butyl-4-methylpyridine were added to 4 ml of methylene chloride and the mixture was stirred at room temperature. Then, 800 mg of pentafluoroethylphenyliodonium trifluoromethanesulfonate was added thereto and the mixture was allowed to react for 30 minutes at room temperature. The reaction mixture was subjected to column chromatography of silica gel and, after eluting iodobenzene with hexane, the product was eluted with diethyl ether. The diethyl ether was distilled off to obtain 319 mg (90% yield) of pentafluoroethylthioacetic acid as an oily substance. 19F-NMR (CCl3F internal standard in CDCl3): -83.98 ppm (t, JCF3,CF2 =3.5 Hz, CF3), -93.39 ppm (q, JCF3,CF2 =3.5 Hz, CF2)

Workup

  1. customto react for 30 minutes at room temperature
  2. washafter eluting iodobenzene with hexane
  3. washthe product was eluted with diethyl ether
  4. distillationThe diethyl ether was distilled off

Sources & evidence

ORD record
ord-673309507f5b4cde8c652f74427d1434
Source dataset
uspto-grants-1983_02
Patent number
US04371710

Reaction notes

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