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Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl(E)-3-(3-fluoro-4-hydroxyphenyl)acrylate

HRID 250834
ノート
印刷プレビュー

反応式

HRID 250834 の反応式
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[OH:34])[CH:29]=O>C1(C)C=CC=CC=1.O>[F:25][C:26]1[CH:27]=[C:28](/[CH:29]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])[CH:31]=[CH:32][C:33]=1[OH:34]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 5872503-Fluoro-4-hydroxybenzaldehyde

生成物 1

HCID 67273036methyl(E)-3-(3-fluoro-4-hydroxyphenyl)acrylate収率 78%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

13.1 g (0.039 mol, 2.2 eq) of methyl (triphenylphosphoranylidene)acetate are added to a solution of 2.5 g (0.0178 mol, 1 eq) of 3-fluoro-4-hydroxybenzaldehyde in 30 ml of toluene. The reaction mixture is heated at 80° C. for 2 hours. The reaction medium is hydrolyzed in water and extracted with ethyl acetate. The organic phases are combined, washed with water and dried over sodium sulfate. The solvent is evaporated off and the oil obtained is chromatographed on silica gel (70/30 heptane/ethyl acetate). 2.7 g of methyl (E)-3-(3-fluoro-4-hydroxyphenyl)acrylate are obtained in solid form. Yield=78%

後処理

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is evaporated off
  5. customthe oil obtained
  6. customis chromatographed on silica gel (70/30 heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-fdc3e6ec1a6d4b1584942ea9e128b919
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07863332B2

反応ノート

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