Ethyl bromoacetate → HCID 22125538, compound

HRID 1858018Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[NH:8][CH:7]=[N:6][C:5]=1[CH:9]=[O:10].Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C1COCC1>[CH:9]([C:5]1[N:6]=[CH:7][N:8]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:4]=1[CH3:3])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A 30% solution of sodium hydride (1.2 g, 32.6 mmol) was washed with pet ether (3×15 mL) and then slurried in THF (30 mL) under nitrogen. The slurry was cooled to 0° C. and 5-methylimidazole-4-carboxaldehyde (3 g, 27.2 mmol) was added in two portions. The mixture was stirred at ambient temperature for 2 hours, cooled to 0° C. and ethyl bromacetate (4.5 mL, 38.1 mmol) was added dropwise. The mixture was stirred at ambient temperature for 40 minutes and partitioned between ethyl acetate and water. The organic layer was isolated, washed with water, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was triturated with pet ether to provide ethyl 4-formyl-5-methylimidazol-1-ylacetate (5.3 g, 27 mmol) as a yellow solid. 1H-NMR (300 Mhz, DMSO-d6): 1.2 (t, 3H), 2.4 (s, 3H), 4.2 (q, 2H), 5.0 (s, 2H), 7.8 (s, 1H), 9.8 (s, 1H).

Workup

temperaturecooled to 0° C.
stirringThe mixture was stirred at ambient temperature for 40 minutes
custompartitioned between ethyl acetate and water
customThe organic layer was isolated
washwashed with water
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was triturated with pet ether

Sources & evidence

ORD record: ord-13289a9f29e34deda3c66f77ceaf14f8
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150379

Reaction notes

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