Diethyl Ether → HCID 86714641, compound

HRID 1409371Notes

Reaction equation

C([C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:7]=[N:6][CH:5]=1)(=O)C.C[Si]([N-][Si](C)(C)C)(C)C.[Li+:25].[C:26]([O:33][CH2:34][CH3:35])(=[O:32])[C:27]([O:29]CC)=O.[CH2:36]([O:38]CC)[CH3:37]>>[CH2:9]([N:8]1[CH:4]=[C:5]([C:36](=[O:38])/[CH:37]=[C:27](\[O-:29])/[C:26]([O:33][CH2:34][CH3:35])=[O:32])[N:6]=[CH:7]1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1.[Li+:25]

Participants

Reactant 4

HCID 3283Diethyl Ether

HCID 7268Diethyl Oxalate

HCID 2733832Lithium Hexamethyldisilazide

HCID 116153681-(1-Benzyl-1H-imidazol-5-yl)ethan-1-one

Product 1

HCID 86714641HCID 86714641, compound

Conditions

Temperature: -75 °C

Procedure

5-Acetyl-1-benzylimidazole (24.97 mmol, 5 g) was dissolved in dry diethyl ether (100 ml) under nitrogen atmosphere. The mixture was cooled to −75° C. and lithium bis(trimethylsilyl)amide (27.5 mmol, 27.5 ml) was added dropwise. The resulting mixture was stirred at −75° C. for an hour. Diethyl oxalate (32.5 mmol, 4.74 g) was added and the mixture was allowed to warm to ambient temperature after which the mixture was stirred for a day at RT. The formed precipitate was removed by filtration and the precipitate was washed with diethyl ether. The precipitate was dried under vacuum. 7.38 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.22 (t, 3H), 4.11 (q, 2H), 5.61 (s, 2H), 6.17 (s, 1H), 7.15-7.31 (m, 5H), 7.48 (d, 1H), 7.88 (d, 1H).

Workup

temperatureto warm to ambient temperature after which the mixture
stirringwas stirred for a day at RT
customThe formed precipitate was removed by filtration
washthe precipitate was washed with diethyl ether
customThe precipitate was dried under vacuum

Sources & evidence

ORD record: ord-161d3bfe1b4948f4bd5da01f2692f793
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921378B2

Reaction notes

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