Iodine → HCID 9992273, compound

HRID 963012Notes

Reaction equation

HRID 963012 reaction equation
N([Si](C)(C)C)=[N+]=[N-].[CH3:8][C:9]1([CH3:16])[CH2:14][CH2:13][C:12](=[O:15])[CH:11]=[CH:10]1.[I:17]I>N1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[I:17][C:11]1[C:12](=[O:15])[CH2:13][CH2:14][C:9]([CH3:16])([CH3:8])[CH:10]=1

Participants

7

Reactant 3

HCID 807IodineHCID 78378AzidotrimethylsilaneHCID 1368392-Cyclohexen-1-one, 4,4-dimethyl-

Product 1

HCID 9992273HCID 9992273, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Freshly distilled azidotrimethylsilane (4.61 mL, 34.7 mmol) was added to a stirred solution of 4,4-dimethyl-2-cyclohexen-1-one (available from Aldrich Chemical Co., 3.04 mL, 23.2 mmol) and dichloromethane (35 mL) at 0° C. under argon. The solution was stirred for 2 hours at 0° C. before adding a solution of iodine (11.8 g, 46.3 mmol) in 35 mL of pyridine and 35 mL of dichloromethane. The resulting solution was stirred for 20 hours at room temperature, diluted with ethyl acetate, and was washed with 20% aqueous Na2S2O3, and 10% aqueous HCl, and water, and brine. The solvents were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (7:1, hexanes:ethyl acetate) to give the title compound as a yellow oil.

Workup

  1. stirringThe resulting solution was stirred for 20 hours at room temperature
  2. washwas washed with 20% aqueous Na2S2O3, and 10% aqueous HCl, and water, and brine
  3. dry with materialThe solvents were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (7:1, hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-1c0c37f417a44a78ae5edb8355a178bb
Source dataset
uspto-grants-1998_06
Patent number
US05760276

Reaction notes

Loading…