Propanedioic acid, monoethyl ester → HCID 67267545, compound

HRID 598169Notes

Reaction equation

HRID 598169 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([O-:5])=O.C[Mg]Br.Cl.[Br:14][C:15]1[N:16]=[CH:17][N:18]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[CH3:30])[C:19]=1C(Cl)=O>C1COCC1>[Br:14][C:15]1[N:16]=[CH:17][N:18]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=2[CH3:30])[C:19]=1[C:3](=[O:5])[CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 3595298Propanedioic acid, monoethyl esterHCID 86613894HCID 86613894, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 67267545HCID 67267545, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.6 mL (14 mmol) of mono-ethyl malonate in 35 mL of THF at 0° C. was added 9.3 mL (28 mmol) of 3.0 M methyl magnesium bromide (ether solution). The dianion solution was stirred for 30 min before adding 1.2 g (3.5 mmol) of 4-bromo-1-(2,4-dimethylphenyl)-1H-imidazole-5-carbonyl chloride hydrochloride in 50 mL of THF dropwise. The cooling bath was then removed and the mixture was allowed to stir at room temperature for 3 h. The reaction was quenched by pouring onto ice and was extracted with ethyl acetate after neutralizing to pH 7 with saturated ammonium chloride. The combined extracts were washed with brine, dried over sodium sulfate, filtered and the resulting filtrate was concentrated to an oil. The oil was purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 1.2 g (94%) of the title compound as a viscous golden oil.

Workup

  1. customThe cooling bath was then removed
  2. stirringto stir at room temperature for 3 h
  3. customThe reaction was quenched
  4. additionby pouring onto ice
  5. extractionwas extracted with ethyl acetate
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe resulting filtrate was concentrated to an oil
  10. customThe oil was purified by flash chromatography
  11. washeluting with a 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-b275578320dc452aaedb6c91016f706e
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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