Ethyl chloroformate → HCID 18516105, compound

HRID 1977413Notes

Reaction equation

HRID 1977413 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Cl:16])[CH:15]=1.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)C>[Cl:9][C:10]1[CH:11]=[N:12][CH:13]=[C:14]([Cl:16])[C:15]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

7

Reactant 4

HCID 10928Ethyl chloroformateHCID 171533,5-DichloropyridineHCID 516892Sodium BicarbonateHCID 2724682Lithium diisopropylamide

Product 1

HCID 18516105HCID 18516105, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of lithium diisopropylamide (45 mL, 1.5 M in THF, 67.6 mmol) in 150 mL THF at −78° C. is treated with 3,5-dichloropyridine (10 g, 67.6 mmol) in 40 mL THF over 1.5 hours, stirred for 1 hour at −78° C., treated with ethyl chloroformate (9.5 mL, 100 mmol), stirred for 2 hours, transferred into saturated sodium bicarbonate (200 ml) at 0° C., treated with diethyl ether (200 ml), and extracted with ethyl ether (2×100 mL). The extract is washed sequentially with saturated sodium bicarbonate solution (2×100 mL), brine (2×100 mL), dried (MgSO4), and concentrated. The residue is purified by flash chromatography on silica gel with hexane/ethyl acetate to provide the title compound.

Workup

  1. stirringstirred for 2 hours
  2. extractionextracted with ethyl ether (2×100 mL)
  3. washThe extract is washed sequentially with saturated sodium bicarbonate solution (2×100 mL), brine (2×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified by flash chromatography on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-4715bbb402424bfa8f21898f6f50bc76
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

Loading…