Sodium Iodide → HCID 58242509, compound

HRID 221110Notes

Reaction equation

[I-].[Na+].Cl[Si](C)(C)C.[CH3:8][C:9](=[O:14])[CH2:10][C:11](=[O:13])[CH3:12].[CH2:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)[CH3:16].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH2:15]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][CH:10]([C:9](=[O:14])[CH3:8])[C:11](=[O:13])[CH3:12])=[CH:19][CH:18]=1)[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of sodium iodide (15.0 g) in acetonitrile (100 ml) was cooled to 0° C. under argon atmosphere, and thereto were added dropwise chlorotrimethylsilane (12.7 ml), 2,4-pentanedione (2.05 ml) and 4-ethylbenzaldehyde (2.68 g), successively. The reaction mixture was stirred at room temperature for 17 hours, and further stirred at 60° C. for 10 hours. The reaction mixture was cooled to room temperature and poured into an aqueous sodium thiosulfate solution. The mixture was extracted with diethyl ether, and the extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 3-(4-ethylphenylmethyl)-2,4-pentanedione (2.72 g) as pale yellow oil. APCI-Mass m/Z 219 (M+H).

Workup

stirringfurther stirred at 60° C. for 10 hours
temperatureThe reaction mixture was cooled to room temperature
extractionThe mixture was extracted with diethyl ether
washthe extract was washed with brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-0404a4cd9ff84521b5e62c613a8dc615
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202984B2

Reaction notes

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