Diethyl Oxalate → HCID 57565017, compound

HRID 1726897Notes

Reaction equation

HRID 1726897 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.[CH2:11]([O:18][CH2:19][C:20]([O:22]CC)=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br.[CH2:28]([N:32]1[CH2:36][CH2:35][N:34]=[C:33]1[NH2:37])[CH2:29][CH2:30][CH3:31]>>[CH2:11]([O:18][C:19]1[C:20](=[O:22])[N:34]2[CH2:35][CH2:36][N:32]([CH2:28][CH2:29][CH2:30][CH3:31])[C:33]2=[N:37][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 69029123HCID 69029123, compound

Product 1

HCID 57565017HCID 57565017, compoundYield 38.2%

Procedure

Reaction of the adduct of diethyl oxalate (5.71 g, 39.1 mmol), ethyl benzyloxyacetate (7.59 g, 39.1 mmol) and sodium hydride (1.71 g of a 60% dispersion in mineral oil, 42.7 mmol) with 1-butyl-4,5-dihydro-1H-imidazol-2-amine hydrobromide (8.68 g, 39.1 mmol) as described for intermediate 1 gave 5.55 g (38% yield) of the title ester as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 0.98 (3H, t, J=7.5 Hz, CH3), 1.31 (3H, t, J=7.1 Hz, CH3), 1.39 (2H, m, CH2), 1.56-1.63 (2H, m, CH2), 3.41 (2H, t, J=7.4 Hz, CH2), 3.69 (2H, t, J=8.9 Hz, CH2), 4.12 (2H, t, J=8.9 Hz, CH2), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.09 (2H, s, OCH2), 7.3-7.4 (3H, m, aromatics), 7.49 (2H, m, aromatics). MS (ESI+) m/e 372 [M+H+].

Sources & evidence

ORD record
ord-a7b6c8b4b8a74a1dbbac07b3a27ec6a9
Source dataset
uspto-grants-2009_02
Patent number
US07494984B2

Reaction notes

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