p-Toluenesulfonic acid → HCID 54356888, compound

HRID 2083790Notes

Reaction equation

HRID 2083790 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C@@H:15]([CH:16]=[CH:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[OH:25])[CH3:2].[C:27](OC(=O)C)(=[O:29])[CH3:28].[C:34](Cl)(=[O:36])[CH3:35].C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@@H:11]1[C:15](=[CH:16][CH:17]=[C:18]([O:24][C:27](=[O:29])[CH3:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:13][C@H:12]1[O:25][C:34](=[O:36])[CH3:35])[CH3:2]

Participants

6

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6367Acetyl chlorideHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 70616058HCID 70616058, compound

Product 1

HCID 54356888HCID 54356888, compound

Procedure

A mixture of 0.5 g 9β-hydroxy-15-oxo-13-prostenoic acid ethyl ester, 5 ml. acetic anhydride, 2 ml. acetyl chloride and 0.52 g. p-toluenesulfonic acid is heated for 3 hours, with the exclusion of moisture, at 100°; poured, after cooling, into 100 ml. ice water containing 15 g. NaHCO3 ; and extracted twice with 50 ml. amounts of diethyl ether. The organic extract is washed until neutral with water, and dried over Na2SO4. After removal of the solvent and chromatographic purification (silica gel/petroleum ether/diisopropyl ether:triethylamine = 100:100:1), 9β,15-diacetoxy-12,14-prostadienoic acid ethyl ester is obtained. UV; 243-244 nm (ε = 19800).

Workup

  1. additionpoured
  2. temperatureafter cooling, into 100 ml
  3. extractionand extracted twice with 50 ml
  4. extractionThe organic extract
  5. washis washed until neutral with water
  6. dry with materialdried over Na2SO4
  7. customAfter removal of the solvent and chromatographic purification (silica gel/petroleum ether/diisopropyl ether:triethylamine = 100:100:1)

Sources & evidence

ORD record
ord-eb06e122ee36481ba145e6ccf09fee90
Source dataset
uspto-grants-1978_04
Patent number
US04086362

Reaction notes

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