Acetone → HCID 18594874, compound

HRID 1580233Notes

Reaction equation

HRID 1580233 reaction equation
CS(O[CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(=O)=O.[CH3:31][C:32](C)=[O:33].[S:35]1C=CC=C1CC([O-])=O.[K+]>O>[C:32]([S:35][CH:6]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[O:25])[CH2:11][CH2:10]1)(=[O:33])[CH3:31]

Participants

5

Reactant 3

HCID 180AcetoneHCID 18594876HCID 18594876, compoundHCID 23696799Potassium 2-thienylacetate

Product 1

HCID 18594874HCID 18594874, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1 g. of ethyl 15-methanesulfonyloxy-9-oxo-prostanoate (Example 90) in 50 ml. of acetone containing 735 mg. of purified potassium thiolacetate is kept at the reflux temperature for 2 hours, then at room temperature for 18 hours. The mixture is diluted with water and the resulting solution is washed with saturated sodium chloride solution, dried with magnesium sulfate and taken to dryness. The residue is chromatographed on silica gel to give an oil; λmax. 5.78 (ring carbonyl and ester group) and 5.92 μ (acetylthio group).

Workup

  1. washthe resulting solution is washed with saturated sodium chloride solution
  2. dry with materialdried with magnesium sulfate
  3. customThe residue is chromatographed on silica gel
  4. customto give an oil

Sources & evidence

ORD record
ord-b9b8a974cc4741b7a1803036e3f2b74b
Source dataset
uspto-grants-1976_01
Patent number
US03932472

Reaction notes

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