Diethyl Carbonate → HCID 69967939, compound

HRID 1108893Notes

Reaction equation

HRID 1108893 reaction equation
C([N:8]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13](C)[N:12]=1)[CH2:9][CH3:10])(OC(C)(C)C)=O.C(=O)([O:22][CH2:23][CH3:24])OCC>C1COCC1>[CH2:9]([NH:8][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH:23]([OH:22])[CH3:24])[N:12]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7766Diethyl CarbonateHCID 21257568HCID 21257568, compound

Product 1

HCID 69967939HCID 69967939, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-(N-Boc-N-ethylamino)-6-pyridylacetate LDA (0.018 mol) was prepared in THF (30 mL), cooled to -78° C., and 2-(N-Boc-N-ethylamino)-6-picoline (3.5 g, 15 mmol) was added, forming a deep red solution. After 15 min, diethyl carbonate (2.2 mL, 17.9 mmol) was added, the burgundy-colored solution was stirred at -78° C. for an additional 15 min, then the reaction was quenched with saturated NH4Cl. The mixture was warmed to RT and extracted with EtOAc(3×30 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. Silica gel chromatography (10% EtOAc/hexane) gave the title compound as colorless oil: MS (ES) m/e 309 (M+H)+.

Workup

  1. customforming a deep red solution
  2. customthe reaction was quenched with saturated NH4Cl
  3. temperatureThe mixture was warmed to RT
  4. extractionextracted with EtOAc(3×30 mL)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-163dda7eef9247b6b9d8b2c63edf80bf
Source dataset
uspto-grants-2000_05
Patent number
US06069158

Reaction notes

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