Sodium Iodide → HCID 131729084, compound

HRID 2070233Notes

Reaction equation

HRID 2070233 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]([S:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)=[O:6].[I-:15].[Na+]>C(#N)C>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([S:7][C:5]([O:4][CH2:3][CH2:2][I:15])=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131730048HCID 131730048, compound

Product 1

HCID 131729084HCID 131729084, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A 50 mL, three-neck, round-bottomed flask equipped with a magnetic stir bar, a reflux condenser, an internal thermometer, and a nitrogen inlet was charged with chloro-ester D1 (2 g, 8 mmol) and sodium iodide (1.8 g, 12 mmol) in acetonitrile (10 mL). The resulting slurry was warmed to 50° C. for 36 hours. The reaction mixture was cooled to room temperature and inorganic solids were removed by filtration. The clear organic phase was concentrated to give a viscous oil. The crude product was purified by column chromatography using ethyl acetate and hexane to give the title compound E4b as a viscous-oil (1 g, ˜30% yield). 1H NMR (CDCl3, 400 MHz): δ 2.31 (d, J=5.6 Hz, 3H), 2.47 (s, 3H), 6.80 (q, J=6 Hz, 1H), 7.11 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.8 Hz, 2H).

Workup

  1. customA 50 mL, three-neck, round-bottomed flask equipped with a magnetic stir bar, a reflux condenser
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custominorganic solids were removed by filtration
  4. concentrationThe clear organic phase was concentrated
  5. customto give a viscous oil
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-96317eb6e7c94dcc9e231df26bcdd66a
Source dataset
uspto-grants-2012_10
Patent number
US08299291B2

Reaction notes

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