Trifluoroacetic acid → HCID 19878787, compound

HRID 1885507Notes

Reaction equation

HRID 1885507 reaction equation
CSCCCCCCC([S:15]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)(=[O:17])=[O:16])C(OCC)=O.F[C:26](F)(F)[C:27]([O:29]O)=[O:28].C[CH:34]([CH2:49][CH2:50][CH2:51]C)[CH2:35][CH:36]([S:40]([C:43]1C=CC=CC=1)(=[O:42])=[O:41])C([O-])=O.F[C:54](F)(F)[C:55](O)=O>>[CH3:43][S:40]([CH2:36][CH2:35][CH2:34][CH2:49][CH2:50][CH2:51][CH:26]([S:15]([C:18]1[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=1)(=[O:16])=[O:17])[C:27]([O:29][CH2:54][CH3:55])=[O:28])(=[O:41])=[O:42]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 10290812Trifluoroperacetic acidHCID 19878771HCID 19878771, compoundHCID 131717519HCID 131717519, compound

Product 1

HCID 19878787HCID 19878787, compound

Procedure

A mixture of 4.0 g. (10.7 mmole) ethyl 8-methylthio-2-(4-methylphenylsulphonyl)-octanoate, 5.35 ml of a 4 molar solution of trifluoroperacetic acid in trifluoroacetic acid and 7.5 ml. trifluoroacetic acid is stirred for 4 hours at 0° c. The solvent is then distilled off in a vacuum and the residue taken up in diethyl ether. This solution is washed with aqueous sodium hydrogen carbonate, dried and evaporated. The residue is chromatographed with a mixture of toluene and dioxan (5:1 v/v) on silica gel to give 3.2 g. (60% of theory) ethyl 8-methylsylphonyl-2-(4-methylphenylsulphonyl-octanoate in the form of a colourless oil.

Workup

  1. additionA mixture of 4.0 g
  2. distillationThe solvent is then distilled off in a vacuum
  3. washThis solution is washed with aqueous sodium hydrogen carbonate
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed with a mixture of toluene and dioxan (5:1 v/v) on silica gel
  7. customto give 3.2 g

Sources & evidence

ORD record
ord-e0a9a36581d8461e93eb9bad9621d01a
Source dataset
uspto-grants-1992_09
Patent number
US05145611

Reaction notes

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