Nitrogen → HCID 59590904, compound

HRID 2098975Notes

Reaction equation

HRID 2098975 reaction equation
C(=O)=O.[CH3:4][C:5](C)=O.N#N.C([Zn]CC)C.[CH3:15][O:16][C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][CH2:22][C:23]2=[C:26]2[C:31](=[O:32])[O:30][C:29]([CH3:34])([CH3:33])[O:28][C:27]2=[O:35])=[CH:19][CH:18]=1>COCCOC.FC(F)(F)S([O-])(=O)=O.[Cu+2].FC(F)(F)S([O-])(=O)=O>[CH2:4]([C:23]1([CH:26]2[C:27](=[O:35])[O:28][C:29]([CH3:33])([CH3:34])[O:30][C:31]2=[O:32])[C:24]2[C:20](=[CH:19][CH:18]=[C:17]([O:16][CH3:15])[CH:25]=2)[CH2:21][CH2:22]1)[CH3:5]

Participants

7

Reactant 4

HCID 947Nitrogen2×HCID 18522661Acetone cardiceHCID 44550512HCID 44550512, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 59590904HCID 59590904, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 2734996copper(II) trifluoromethanesulfonateCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A 200 mL round bottom flask was charged with copper(II) trifluoromethanesulfonate (0.087 g, 0.24 mmol) and DME (12 mL), cooled to −40° C. (dry ice/acetone), and subjected to 3 cycles of evacuation/back-filling with N2. To the cold solution were added diethylzinc (1.0 M solution in hexanes, commercially available from Aldrich) (12 mL, 12 mmol) and a solution of 18.1 (0.694 g, 2.4 mmol) in DME (12 mL) slowly under N2. The mixture was warmed to room temperature and stirred for 2 days. The reaction was carefully quenched with 1 N HCl (15 mL) and diluted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4) and concentrated. The residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes) to afford 42.1 (0.31 g, 40% yield) as a yellow oil.

Workup

  1. customThe reaction was carefully quenched with 1 N HCl (15 mL)
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cea9ad03907a428d93a0dfb7473a9256
Source dataset
uspto-grants-2013_05
Patent number
US08450522B2

Reaction notes

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