Propan-2-one--water (1/1) → HCID 22177240, compound

HRID 1797169Notes

Reaction equation

HRID 1797169 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH:12]=C)[C:9]#[N:10])=[CH:4][CH:3]=1.CC(C)=[O:16].O>O.O=[Os](=O)(=O)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][CH:12]=[O:16])[C:9]#[N:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 18366337Propan-2-one--water (1/1)HCID 22177251HCID 22177251, compound

Product 1

HCID 22177240HCID 22177240, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-(4-iodo-phenyl)-pent-4-enenitrile (2.8 g, 9.9 mmol, intermediate for preparing EXAMPLE 2), OsO4 (0.7 mL, 4% in water, 0.10 mmol), and NaIO4 (4.44 g, 20.8 mmol) in 2:1 acetone/H2O (100 mL) was stirred at room temperature for 16 h. TLC (1:1 hexanes/EtOAc) showed no starting material left. The mixture was diluted with H2O (50 mL) and extracted with CH2Cl2 (50 mL×4). The organic layer was washed with brine, dried (Na2SO4) and concentrated by rotary evaporation. Purification by silica gel chromatography (1:1 hexanes/EtOAc) gave 2-(4-iodo-phenyl)-4-oxo-butyronitrile as a yellowish oil, 1.9 g (68%). 1H NMR (300 MHz, CDCl3): δ 9.85 (s, 1H), 7.84 (d, 2H), 7.24 (d, 2H), 4.44 (t, 1H), 3.33 (dd, 1H), 3.14 (dd, 1H).

Workup

  1. waitleft
  2. extractionextracted with CH2Cl2 (50 mL×4)
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by rotary evaporation
  6. customPurification by silica gel chromatography (1:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-9a5a256988754675873ccf2050289c78
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

Loading…