Methyl iodide → Methyl 2-(3-nitrophenyl)propanoate

HRID 15845노트

반응식

HRID 15845 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[N+:11]([C:14]1[CH:15]=[C:16]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].I[CH3:26].[Cl-].[NH4+]>C1COCC1>[N+:11]([C:14]1[CH:15]=[C:16]([CH:20]([CH3:26])[C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12]

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 526967Methyl 2-(3-nitrophenyl)acetateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 13054272Methyl 2-(3-nitrophenyl)propanoate수율 33.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of lithium hexamethyldisilazide (1M, hexane, 1.0 eq., 21.5 ml) was added dropwise to a stirred solution of methyl (3-nitrophenyl)acetate (4.2 g) in THF (30 ml) at −30 C. The mixture was warmed to 0 C and re-cooled to −30 C then iodomethane (1.0 equiv., 3.0 g.) was added. The solution was warmed to room temperature and poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated. The crude was purified using chromatography (SiO2, SPE) using cyclohexane/ethyl acetate (80/20) as eluent to afford the title compound as yellow liquid (1.50 g, 30% yield).

후처리

  1. temperatureThe mixture was warmed to 0 C
  2. temperaturere-cooled to −30 C
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude was purified

출처 및 근거

ORD 기록
ord-eab3a07efa654e14a99efe66be30d9ab
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732600B2

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