Potassium bisulfate → 1-(4,5-Diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopentene

HRID 377303Notes

Reaction equation

HRID 377303 reaction equation
O[C:2]1([C:16]2[O:17][C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:20]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=1.S([O-])(O)(=O)=O.[K+]>C1(C)C=CC=CC=1>[C:21]1([C:19]2[N:20]=[C:16]([C:2]3[CH:3]([CH2:7][C:8]4[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[CH:9]=4)[CH2:4][CH2:5][CH:6]=3)[O:17][C:18]=2[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 516920Potassium bisulfateHCID 193585111-Hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane

Product 1

HCID 211965411-(4,5-Diphenyloxazol-2-yl)-5-(3-methoxybenzyl)cyclopenteneYield 104.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentane (8.0 g) in toluene (160 ml) was added potassium hydrogensulfate (2.6 g), and the solution was stirred for 1 hour under reflux. After being cooled, the solution was washed with water, saturated sodium bicarbonate aqueous solution and brine and evaporated in vacuo. The oily residue was chromatographed on silica gel to afford a mixture (8.0 g) of 1-(4,5-diphenyloxazol-2-yl)-5-(3-methoxybenzyl)-cyclopentene and 1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclopentene.

Workup

  1. temperatureunder reflux
  2. temperatureAfter being cooled
  3. washthe solution was washed with water, saturated sodium bicarbonate aqueous solution and brine
  4. customevaporated in vacuo
  5. customThe oily residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-191f60b0ae0943ce9325336ff7c37d9d
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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