p-Toluenesulfonic acid → 1-(4,5-Diphenyloxazol-2-yl)-8-(3-methoxybenzyl)-1-cyclooctene

HRID 1741382Notes

Reaction equation

HRID 1741382 reaction equation
O[C:2]1([C:19]2[O:20][C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:24]1([C:22]2[N:23]=[C:19]([C:2]3[CH:3]([CH2:10][C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=4)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=3)[O:20][C:21]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 183672891-(Hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane

Product 1

HCID 543076321-(4,5-Diphenyloxazol-2-yl)-8-(3-methoxybenzyl)-1-cycloocteneYield 112.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(hydroxy)-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cyclooctane (3.5 g) and p-toluenesulfonic acid (500 mg) in toluene (50 ml) was stirred for 4 hours under reflux. The solution was washed with water, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 1-(4,5-diphenyloxazol-2-yl)-8-(3-methoxybenzyl)-1-cyclooctene (3.8 g). MS (m/z): 450 (M+ +1) IR (Neat): 1600 cm-1NMR (CDCl3, δ): 1.4-2.0.(8H, m), 2.2-2.4 (2H, m), 3.0 (1H, m), 3.2-3.5 (2H, m), 3.78 (3H, s), 6.65 (1H, s), 6.7-7.0 (3H, m), 7.18 (1H, t, J=8 Hz), 7.2-7.8 (11H, m)

Workup

  1. temperatureunder reflux
  2. washThe solution was washed with water, sat. NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1b379c2cfd1448db96ba99d89df9bdd8
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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