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

HRID 21513ノート

反応式

HRID 21513 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24c530ac04374da9b6af1f2e14f1abda
出典データセット
uspto-grants-1995_06
特許番号
US05424280

反応ノート

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