Tetrahydrofuran → HCID 18398699, compound

HRID 1018964Notes

Reaction equation

HRID 1018964 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:20]=[O:21])[CH:6]=[CH:5]2.[CH2:22]([Mg]Br)[CH:23]([CH3:25])[CH3:24].C1COCC1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:20]([OH:21])[CH2:22][CH:23]([CH3:25])[CH3:24])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 18398693HCID 18398693, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 18398699HCID 18398699, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of diethyl 6-bromo-2-formyl-8-quinolylphosphonate (293 mg, 0.78 mmol) in toluene (6 mL) at −10° C. was added a 2M solution of isobutylmagnesium bromide in THF (1.59 mL, 3.12 mmol). The mixture was stirred at −10° C. to −5° C. for 2 h. Aqueous NH4CL was added and the mixture was extracted with EtOAc. The organic extracts were washed with brine, dried (anhyd. MgSO4) and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 179 mg (53%) of the title compound

Workup

  1. additionAqueous NH4CL was added
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (anhyd. MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-49d5be2f8b0949d5998a513277cb21d0
Source dataset
uspto-grants-2002_11
Patent number
US06486141B2

Reaction notes

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