Nitrogen → HCID 57467578, compound

HRID 404311Notes

Reaction equation

HRID 404311 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([F:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=O.[CH3:15]C(C)([O-])C.[K+].N#N>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([F:13])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[CH2:15]

Participants

6

Reactant 3

HCID 947NitrogenHCID 23665647Potassium tert-butoxideHCID 55275462HCID 55275462, compound

Product 1

HCID 57467578HCID 57467578, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A screw-cap vial was charged with H3.3 (0.962 g, 4.85 mmol), methyltriphenylphosphonium bromide (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (2.08 g, 5.83 mmol), and THF (20 mL). To the white slurry was added potassium tert-butoxide (1.0 M in THF) (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (5.83 mL, 5.83 mmol) dropwise under N2. The resulting brown mixture was stirred for 30 minutes at room temperature, quenched with acetone (1 mL) and saturated aqueous NH4Cl, and diluted with EtOAc. The organic layer was washed with water and brine, dried (MgSO4), and concentrated. The residue was suspended in hexanes, filtered, and concentrated, and the initially obtained product was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford H3.4 (0.835 g, 88% yield) as a colorless oil.

Workup

  1. customquenched with acetone (1 mL) and saturated aqueous NH4Cl
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe initially obtained product was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-4948d40c60024a7e86880b1496787f34
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

Loading…