p-Toluenesulfonic acid → HCID 18367246, compound

HRID 1741359Notes

Reaction equation

HRID 1741359 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). MS (m/z): 436 (M+ +1) IR (Neat): 1600 cm-1NMR (CDCl3, δ): 1.3-2.0 (6H, m), 2.4 (2H, m), 2.83 (1H, dd, J=10.0, 14 Hz), 3.00 (1H, dd, J=6.0, 14.0 Hz), 3.78 (3H, s), 6.7-7.0 (3H, m), 7.20 (1H, t, J=8 Hz), 7.2-7.8 (11H, m)

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-11c5bfea123e46f39bf2b2b4f2e70c27
Source dataset
uspto-grants-1999_10
Patent number
US05972965

Reaction notes

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