Iodine → HCID 22002644, compound

HRID 325183Notes

Reaction equation

HRID 325183 reaction equation
[I:1]I.[CH3:3][C:4]1([CH3:10])[CH2:8][C:7](=[O:9])[CH:6]=[CH:5]1>C(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.CCOCC>[CH3:3][C:4]1([CH3:10])[CH2:8][C:7](=[O:9])[C:6]([I:1])=[CH:5]1

Participants

6

Reactant 2

HCID 807IodineHCID 1409554,4-Dimethyl-2-cyclopenten-1-one

Product 1

HCID 22002644HCID 22002644, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent2×HCID 3283Diethyl EtherSolventHCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a cold (4° C.) solution of iodine (4.5 g, 18 mmol) in carbon tetrachloride (15 mL) and pyridine (15 mL), was added over 1 min. a solution of 4,4-dimethyl-2-cyclopenten-1-one (930 mg, 8.4 mmol) in carbon tetrachloride (15 mL) and pyridine (15 mL). The resulting red-brown solution was stirred at r.t. for 22 h. The reaction was diluted with Et2O (200 mL), washed successively with water (50 mL), 1.0 N HCl (50 mL), water (50 mL), and aqueous Na2S2O5 20% w/v, then dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography eluting with 10% EtOAc/hexanes to give the title compound as a white solid.

Workup

  1. washwashed successively with water (50 mL), 1.0 N HCl (50 mL), water (50 mL), and aqueous Na2S2O5 20%
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography
  5. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-2f224a235a5c4ea489ec9d417946ada5
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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