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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2376445Generated: October 27, 2026

p-Toluenesulfonic acid monohydrate → N-(3-(4-Isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide

https://huagongshe.com/reaction/2376445

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acid monohydrateHCID 521998—
ReactantN-(7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamideHCID 23113921—
SolventTolueneHCID 1140—
ProductN-(3-(4-Isopropylphenyl)-4,6-dimethyl-7-vinyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamideHCID 2311398089%

Reaction Conditions

Temperature80 °C

Reaction Steps

A solution of N-(7-(1-hydroxyethyl)-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (1.23 g, 3.02 mmol) obtained in Example 22 and p-toluenesulfonic acid monohydrate (20 mg) in toluene (20 mL) was refluxed with heating at 80° C. for 1 hour under an argon atmosphere. The reaction solution was washed with an aqueous saturated sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9) to obtain 1.09 g (yield: 89%) of the title compound. Melting point: 171-172° C. (hexane-ethyl acetate).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07465815B2
Source datasetuspto-grants-2008_12
ORD IDord-3e6871ff1ca640ec8833ec5fa62d2751
Source noteuspto-grants-2008_12