Water → Methyl {o-[5-(methoxymethoxy)-2-nitrophenoxy]phenoxy}acetate

HRID 21513노트

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HRID 21513 반응식
F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][O:10][CH3:11])[CH:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[OH:15][C:16]1[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=1[O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[CH3:11][O:10][CH2:9][O:8][C:6]1[CH:5]=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[O:15][C:16]1[CH:27]=[CH:26][CH:25]=[CH:24][C:17]=1[O:18][CH2:19][C:20]([O:22][CH3:23])=[O:21]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23202292-(Methoxycarbonyl)methoxyphenolHCID 199324002-Fluoro-4-(methoxymethoxy)-1-nitrobenzene

생성물 1

HCID 54326397Methyl {o-[5-(methoxymethoxy)-2-nitrophenoxy]phenoxy}acetate수율 21.5%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of 2-fluoro-4-(methoxymethoxy)-1-nitrobenzene (9.25 g, 0.046 mol), methyl (o-hydroxyphenoxy)acetate (8.5 g, 0.047 mol) and potassium carbonate (6.44 g, 0.047 mol) in N,N-dimethylformamide is stirred at 100° C. for 18 hours, cooled to room temperature, poured into water and extracted with ether. The organic extract is washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an orange gum. Flash chromatography of the gum using silica gel and a 35% ethyl acetate in hexanes solution gives the title product as a yellow oil (3.6 g) which is identified by 1HNMR and 13CNMR spectral analyses.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. extractionThe organic extract
  4. washis washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an orange gum

출처 및 근거

ORD 기록
ord-24c530ac04374da9b6af1f2e14f1abda
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424280

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