Ethyl chloroformate → HCID 22066065, compound

HRID 2101730Notes

Reaction equation

HRID 2101730 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][N:11]([CH2:21][CH3:22])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:4][CH:3]=1.C([Li])CCC.Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:11]([CH2:21][CH3:22])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 22066069HCID 22066069, compoundHCID 178418339Butyllithium

Product 1

HCID 22066065HCID 22066065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-ethylimidazole (230 mg, 0.66 mmol) from Step A (higher Rf isomer) in THF (4 mL) cooled to −70° C. in a dry ice/acetone bath was added 1.6N n-butyl lithium in hexanes (0.500 mL, 0.80 mmol). The reaction was stirred for 1 hr and then ethyl chloroformate (0.130 mL, 1.3 mmol) was added via syringe. The reaction was allowed to warm to rt for 1 hr and was then quenched with aq. sodium bicarbonate and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by Prep TLC (3×1 mm, silica) (25% ethyl acetate in hexanes) to afford the title compound.

Workup

  1. customwas then quenched with aq. sodium bicarbonate
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by Prep TLC (3×1 mm, silica) (25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f2fd42c4ae674ef28127cad221684564
Source dataset
uspto-grants-2009_08
Patent number
US07572785B2

Reaction notes

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