3-Methoxyphenol → 2-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone

HRID 31305

反応式

HRID 31305 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][C:16]=2[OH:20])=[O:11])[CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 2

HCID 90073-MethoxyphenolHCID 676173-Fluorophenylacetic acid

生成物 1

HCID 179785042-(3-Fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone

反応条件

温度
65 °C

実験手順

(3-Fluorophenyl)acetic acid (3.7 g) and 3-methoxyphenol (3.0 g) were dissolved into BF3Et2O (60 ml, 20 eq) under argon. The mixture was stirred at 60-70° C. until disappearance of the starting materials (9 h) and poured into large volume of ice water. After extraction with ethyl acetate the combined organic layers were washed with water, dried and evaporated. The crude product was purified by column chromatography using CH2Cl2 as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 12.41 (br s, 1H), 8.02 (d, 1H, J 9.0 Hz), 7.34-7.38 (m, 1H), 7.09-7.13 (m, 3H), 6.56 (dd, 1H, J 9.0, 2.5 Hz), 6.49 (d, 1H, J 2.5 Hz), 4.41 (s, 2H), 3.83 (s, 3H).

後処理

  1. extractionAfter extraction with ethyl acetate the combined organic layers
  2. washwere washed with water
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by column chromatography

出典と根拠

ORDレコード
ord-1391c4fde4464f7eb0e82249779eb5ee
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

関連ノート

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