Diethyl Ether → HCID 86714641, compound

HRID 872932Notes

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: -78 °C

Procedure

5-acetyl-1-benzylimidazole (5 g, 24.97 mmol) was dissolved in dry diethyl ether (100 ml). The mixture was cooled to −78° C. with dry ice/acetone-bath. Lithium bis(trimethylsilyl)amide (27.5 ml, 27.5 mmol) was added dropwise and the mixture was stirred at −78° C. for 1 h. Diethyl oxalate (4.41 ml, 32.5 mmol) was added and the reaction mixture was allowed to warm to RT. The following mixture was stirred overnight at RT. The precipitated product was filtered, washed with diethyl ether and dried. 1H-NMR (400 MHz; d6-DMSO): δ, 1.22 (t, 3H), 4.11 (q, 2H), 5.62 (s, 2H), 6.18 (s, 1H), 7.16-7.31 (m, 5H), 7.49 (d, 1H), 7.89 (d, 1H).

Workup

temperatureto warm to RT
stirringThe following mixture was stirred overnight at RT
filtrationThe precipitated product was filtered
washwashed with diethyl ether
customdried

Sources & evidence

ORD record: ord-f9ee8d2830974196945b7255c07c4eec
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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