p-Toluenesulfonic acid → HCID 18367246, compound

HRID 380092Notes

Reaction equation

HRID 380092 reaction equation
O[C:2]1([C:18]2[O:19][C:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:22]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:23]1([C:21]2[N:22]=[C:18]([C:2]3[CH:3]([CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=4)[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]=3)[O:19][C:20]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 18367267HCID 18367267, compound

Product 1

HCID 18367246HCID 18367246, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-hydroxy-1-(4,5-diphenyloxazol-2-yl)-2-(3-methoxybenzyl)cycloheptane (5.2 g) and p-toluenesulfonic acid (500 mg) in toluene (50 ml) was stirred under reflux for 4 hours. 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)-7-(3-methoxybenzyl)-1-cycloheptene (4.7 g).

Workup

  1. temperatureunder reflux for 4 hours
  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-8678b9477c0e4b9d80e1ac972e4f6de8
Source dataset
uspto-grants-2001_10
Patent number
US06300344B1

Reaction notes

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