p-Toluenesulfonic acid → HCID 86737062, compound

HRID 1706859Notes

Reaction equation

HRID 1706859 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][C:17]2([O:26][CH2:25][CH2:24][O:23]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][C:11]1=O.COC(=O)CCCCCCC1C(=O)CCC1C=O.P(=O)([O-])[O:48][CH2:49][C:50]1(OCC[O:58]1)CCCCC(C)C.[H-].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)C.O.C(O)CO.C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C@@H:10]1[C@@H:14]([CH:15]=[CH:16][C:17]23[O:26][CH2:25][CH2:24][O:23][C:18]2([O:48][CH2:49][CH2:50][O:58]3)[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][CH2:12][CH2:11]1

Participants

10

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 24758Sodium hydrideHCID 13941293Methyl 7-(2-formyl-5-oxocyclopentyl)heptanoateHCID 70596212HCID 70596212, compoundHCID 178442547HCID 178442547, compound

Product 1

HCID 86737062HCID 86737062, compound

Reagents, catalysts & solvents 4

HCID 174Ethylene GlycolSolventHCID 241BenzeneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2 g of 9-oxo-15,15-ethylenedioxy-13-prostenoic acid methyl ester (obtainable from 7-(2-formyl-5-oxo-cyclopentyl)-heptanoic acid methyl ester by reaction with dimethyl-2,2-ethylenedioxyheptyl phosphonate in the presence of NaH), 100 ml of dry benzene, 10 ml of ethylene glycol and 0.2 g of p-toluenesulphonic acid is boiled for 12 hours on a water separator. After cooling, the mixture is diluted with 100 ml of diethyl ether and washed with aqueous NaHCO3 solution and water. The organic phase is dried over Na2SO4 and the solvent distilled. After chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9;15,15-bis-(ethylenedioxy)-13-prostenoic acid methyl ester is obtained.

Workup

  1. temperatureAfter cooling
  2. washwashed with aqueous NaHCO3 solution and water
  3. dry with materialThe organic phase is dried over Na2SO4
  4. distillationthe solvent distilled
  5. customAfter chromatographic purification of the residue (silica gel/diisopropyl ether), 9,9

Sources & evidence

ORD record
ord-cceb96c820404e2ea2b7249272bcac2f
Source dataset
uspto-grants-1980_06
Patent number
US04209444

Reaction notes

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