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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 62252Generated: October 25, 2026

p-Toluenesulfonic acid → (E)-2-(2-fluoro-3-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

https://huagongshe.com/reaction/62252

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acidHCID 6101—
Reactant2-Fluoro-3-(trifluoromethyl)benzaldehydeHCID 517978—
Reactant6-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-oneHCID 117940128—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product(E)-2-(2-fluoro-3-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-oneHCID 117940182—

Reaction Conditions

Temperature120 °C

Reaction Steps

To a solution of 13 (100 mg, 0.404 mmol) in toluene 10 mL was added 2-fluoro-3-(trifluoromethyl)benzaldehyde 78 (77.7 mg, 0.404 mmol). PTSA (153.8 mg, 0.809 mmol) was added to the reaction mixture and stirred at 120° C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound 79 which was purified through flash chromatography by using 100-200 mesh silica gel. The compound (E)-2-(2-fluoro-3-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 79 was eluted at 34% ethyl acetate in hexane to afford yellow coloured.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09446047B2
Source datasetuspto-grants-2016_09
ORD IDord-4bad080690fe488c9ed19b38095be50f
Source noteuspto-grants-2016_09