p-Toluenesulfonic acid → HCID 18673927, compound

HRID 1635979Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

To 500 mg of 3-acetyloxy-7-[(5-nitro-2-pyridinyl)oxy]-1H-indene, 5 ml of benzoyl chloride and 15 mg of p-toluenesulfonic acid were added and the mixture was stirred at 100° C. After 1.5 hours, ethyl acetate was added to the reaction solution and the solution was washed in turn with a saturated sodium hydrogencarbonate solution and a saturated sodium chloride solution. The solution extracted with ethyl acetate was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (10:1)) to obtain 130 mg of the titled compound as a white powder.

Workup

washthe solution was washed in turn with a saturated sodium hydrogencarbonate solution
extractionThe solution extracted with ethyl acetate
dry with materialwas dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (10:1))

Sources & evidence

ORD record: ord-c4fdabee3d2b4242ba6bef47b16076e3
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06511995B1

Reaction notes

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