Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 70391665, compound

HRID 247505Notes

Reaction equation

HRID 247505 reaction equation
[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14]([C@@H:15]([O:25]C2CCCCO2)/[CH:16]=[CH:17]/[C:18]([CH3:24])([CH3:23])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([CH3:32])[CH2:12][C:11]1=[O:33].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:8]\[CH2:9][C@@H:10]1[C@@H:14]([C@@H:15]([OH:25])/[CH:16]=[CH:17]/[C:18]([CH3:23])([CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])[C@H:13]([CH3:32])[CH2:12][C:11]1=[O:33]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 70391994HCID 70391994, compound

Product 1

HCID 70391665HCID 70391665, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The crude optically active (5Z,11alpha,13S,14E)-13-(2-tetrahydropyranyloxy)-11,16,16-Tri-methyl-9-oxoprosta-5,14-dien-1-oic acid methyl ester (10.55 g) in methanol (100 mL) solution was treated with pyridinium p-toluenesulfonate (1.0 g) and stirred under argon at 40° for 24 hours. After cooling it, the solution was poured into brine (500 mL) and the product was extracted three times with hexane (150 mL each time). The combined extract was dried over sodium sulfate and stripped of solvent to give 9.5 g (>100%) of optically active (5Z,11alpha,13S,14E)-13-hydroxy-11,16,16-trimethyl-9-oxoprosta-5,14-dien-1-oic acid methyl ester as a yellow oil.

Workup

  1. temperatureAfter cooling it
  2. extractionthe product was extracted three times with hexane (150 mL each time)
  3. extractionThe combined extract
  4. dry with materialwas dried over sodium sulfate

Sources & evidence

ORD record
ord-4a8858986d0b4c1ca188e99fee64d265
Source dataset
uspto-grants-1987_11
Patent number
US04707555

Reaction notes

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