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

HRID 963007

반응식

HRID 963007 반응식
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]

참가 물질

7

반응물 3

HCID 807IodineHCID 145113-Methyl-2-cyclohexen-1-one2회HCID 78378Azidotrimethylsilane

생성물 1

HCID 102431782-Cyclohexen-1-one, 2-iodo-3-methyl-

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a61ddd3ab12e4ddf87f77400f83cae47
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760276

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