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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 340699Generated: October 26, 2026

Acetone → 2-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

https://huagongshe.com/reaction/340699

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetoneHCID 180—
ReactantCyanogen iodideHCID 10478—
Reactant2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneHCID 57781277—
SolventTetrahydrofuranHCID 8028—
Product2-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneHCID 5778127033%

Reaction Conditions

Temperature50 °C

Reaction Steps

2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (1.87 g, 10.0 mmol), acetone (3.68 mL, 50.0 mmol) and ICN Alumina B (manufactured by ICN, Akt.1, 20 g) were suspended in tetrahydrofuran (50 mL), and the mixture was stirred at 50° C. for 9 hr. Acetone (3.68 mL, 50.0 mmol) was added, and the mixture was further stirred for 12 hr. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50) to give the title compound (742 mg, yield 33%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08895591B2
Source datasetuspto-grants-2014_11
ORD IDord-5867e73276d34257a09adf3241cd1117
Source noteuspto-grants-2014_11