Sodium Bicarbonate → HCID 67367135, compound

HRID 1753193Notes

Reaction equation

HRID 1753193 reaction equation
[Cl-].[Cl-].[NH3+:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][NH+:10]=[CH:9][CH:8]=1)=[O:6].CO[C:15]1([C:22](OC)=O)[CH2:19][CH2:18][CH:17]([O:20][CH3:21])[O:16]1.C([O-])(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)Cl>[O:6]=[C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[CH2:4][N:3]1[CH:22]=[CH:15][CH:19]=[C:18]1[C:17]([O:20][CH3:21])=[O:16]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 13152840Methyl 2,5-dimethoxyoxolane-2-carboxylateHCID 87373563HCID 87373563, compound

Product 1

HCID 67367135HCID 67367135, compoundYield 11.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(ammonioacetyl)pyridinium dichloride (crude, 100 mg, 0.48 mmol), methyl 2,5-dimethoxytetrahydrofuran-2-carboxylate (99 mg, 0.52 mmol) and sodium acetate (157 mg, 1.9 mmol) were suspended in glacial acetic acid (1.5 mL) and the mixture heated at 100° C. After 4.5 hours the dark mixture was allowed to cool to room temperature and ice (5 g) was added. The mixture was neutralised with solid NaHCO3 and allowed at room temperature. The resulting suspension was diluted with CH2Cl2 (5 mL), filtered and the aqueous layer extracted with CH2Cl2 (3×5 mL). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield a brown oil that was purified by flash chromatography (Biotage SP4 (4 g cartridge, gradient hexanes 3 CV, 0-100% EtOAc in hexanes 15 CV, hold for 5 CV) to give methyl 1-[2-oxo-2-(pyridin-4-yl)ethyl]-1H-pyrrole-2-carboxylate (13 mg, yield 11%). ESI-MI m/z [M+H]+ 245.1.

Workup

  1. temperatureto cool to room temperature
  2. customallowed at room temperature
  3. filtrationfiltered
  4. extractionthe aqueous layer extracted with CH2Cl2 (3×5 mL)
  5. dry with materialThe organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield a brown oil that
  9. customwas purified by flash chromatography (Biotage SP4 (4 g cartridge, gradient hexanes 3 CV, 0-100% EtOAc in hexanes 15 CV, hold for 5 CV)

Sources & evidence

ORD record
ord-69046f8bf9b74ee798b036c588b0a9ba
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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