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

HRID 340699

Reaction equation

[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:15][C:16]([CH3:18])=O.IC#N>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[O:14])[C:11](=[C:16]([CH3:18])[CH3:15])[CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

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%).

Workup

stirringthe mixture was further stirred for 12 hr
filtrationThe reaction solution was filtered
customthe filtrate was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50)

Sources & evidence

ORD record: ord-5867e73276d34257a09adf3241cd1117
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895591B2

Linked notes

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