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

HRID 1661401

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-2dc00c06fd124a3eb56985a998ad17be
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030337B2

Linked notes

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