Sodium Iodide → 4-Cyano-5-methyl-4-phenylhexyl Iodide

HRID 1582762노트

반응식

HRID 1582762 반응식
[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6]O)#[N:2].S(Cl)(C)(=O)=O.[I-:22].[Na+]>C(#N)C.C(N(CC)CC)C>[C:1]([C:3]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH:8]([CH3:10])[CH3:9])[CH2:4][CH2:5][CH2:6][I:22])#[N:2]

참가 물질

6

반응물 3

HCID 5238Sodium IodideHCID 31297Methanesulfonyl chlorideHCID 101306314-Cyano-5-methyl-4-phenylhexanol

생성물 1

HCID 223936654-Cyano-5-methyl-4-phenylhexyl Iodide

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8471Triethylamine용매

실험 절차

5.00 g 23.0 mmol of 4-Cyano-5-methyl-4-phenylhexanol disclosed in Example 2 or 3 of JP 11-70613-A was added to and dissolved in acetonitrile 150 ml and triethylamine 3.53 ml. Mesyl chloride, 1.96 ml 25.3 mmol, was added thereto. After 25 minutes, sodium iodide 20.7 g was added thereto. The reaction mixture was partitioned by adding brine and ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate and then with brine, dried over magnesium sulfate, and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 5. 89 g 18.0 mmol, 78.2%, was obtained as a pale yellow oil.

후처리

  1. additionwas added to and
  2. customThe reaction mixture was partitioned
  3. additionby adding brine and ethyl acetate
  4. washThe organic layer was washed with aqueous sodium thiosulfate
  5. dry with materialwith brine, dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane system), whereby the title compound, 5
  8. custom89 g 18.0 mmol, 78.2%, was obtained as a pale yellow oil

출처 및 근거

ORD 기록
ord-ee1d669f9bff4bacb42ff89245eaa878
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06737425B1

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