p-Toluenesulfonic acid → HCID 86639390, compound

HRID 1685807Notes

Reaction equation

HRID 1685807 reaction equation
[OH:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](O)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:1][CH:2]2[CH2:6][S:5][CH2:4][CH:3]2[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])=[CH:10][CH:9]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 24782884HCID 24782884, compound

Product 1

HCID 86639390HCID 86639390, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-[4-(4-Hydroxythiolan-3-ylmethyl)phenyl]propionic acid (1.0 g) obtained in Example 9 was dissolved in toluene (30 ml), and p-toluenesulfonic acid (710 mg) was added to the solution and refluxed by heating for 5 hours. After completion of the reaction, the reaction mixture was quenched with water, and the organic layer was separated, and washed with water and saturated brine. Then, the solvent was evaporated under reduced pressure to give a crude product of 2-{4-[4-(4-toluenesulfonyloxy)thiolan-3-ylmethyl]phenyl}propionic acid (700 mg). A part of the product (474 mg) was dissolved in tetrahydrofuran (4.0 ml), and potassium tert-butoxide (506 mg) was added to the solution, and refluxed by heating for 5 hours. After completion of the reaction, the reaction mixture was acidified with 2.0 M aqueous hydrochloric acid under ice cooling, and then extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) to give the title compound (90 mg, 14.4% for 2 steps).

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 5 hours
  3. customAfter completion of the reaction
  4. customthe reaction mixture was quenched with water
  5. customthe organic layer was separated
  6. washwashed with water and saturated brine
  7. customThen, the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89da9a3f832440bab5bd905a0fe82077
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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