Iodine → 2-Cyclohexen-1-one, 2-iodo-3-methyl-

HRID 963007Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Freshly distilled azidotrimethylsilane (2.65 mL, 20 mmol) was added to a stirred solution of 3-methyl-2-cyclohexen-1-one (Compound 1, 1.13 mL, 10 mmol) and dichloromethane (15 mL) at 0° C. under argon. The solution was stirred for 2 hours at 0° C. before adding a solution of iodine (5.08 g, 20 mmol) in 15 mL of pyridine and 15 mL of dichloromethane. The resulting solution was stirred for 4 hours at room temperature, diluted with ethyl acetate, and was washed successively with 20% aqueous Na2S2O3, 10% aqueous HCl, water, and brine. The solvents were dried (MgSO4) 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

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

Sources & evidence

ORD record: ord-a61ddd3ab12e4ddf87f77400f83cae47
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05760276

Reaction notes

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