Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → (E)-3-(3-Chloro-benzo[b]thiophen-2-yl)-acrylic acid methyl ester

HRID 406796ノート

反応式

HRID 406796 の反応式
[Cl:1][C:2]1[C:3]2[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=2[S:5][C:6]=1[CH:7]=O.[CH3:13][O:14][C:15](=[O:36])[CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[CH3:13][O:14][C:15](=[O:36])/[CH:16]=[CH:7]/[C:6]1[S:5][C:4]2[CH:9]=[CH:10][CH:11]=[CH:12][C:3]=2[C:2]=1[Cl:1]

参加物

5

反応物 3

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 516892Sodium BicarbonateHCID 8181213-Chloro-1-benzothiophene-2-carbaldehyde

生成物 1

HCID 46825722(E)-3-(3-Chloro-benzo[b]thiophen-2-yl)-acrylic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 3.52 g (18.3 mmol) of 13 in 50 mL toluene was treated with methyl(triphenylphosphoranylidene)acetate (7.48 g, 21.9 mmol). After 4 h, saturated NaHCO3 solution (50 mL) was added and the mixture extracted with ethyl acetate (2×75 mL). The combined ethyl acetate solution was washed with brine (50 mL), dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (5% ethyl acetate/hexane) provided 3.60 g (14.6 mmol, 80%) of the enoate (14).

後処理

  1. extractionthe mixture extracted with ethyl acetate (2×75 mL)
  2. washThe combined ethyl acetate solution was washed with brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography on silica gel (5% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-824feff9e81248b8b464da03e37175b7
出典データセット
uspto-grants-2014_06
特許番号
US08754122B2

反応ノート

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