Sodium Carbonate → (E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

HRID 984316ノート

反応式

HRID 984316 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[CH3:15])=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>COCCOC.Cl>[CH2:13]([O:12][C:10](=[O:11])/[CH:9]=[C:8](/[C:5]1[CH:6]=[CH:7][C:2]([C:26]2[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=2)=[CH:3][CH:4]=1)\[CH3:15])[CH3:14]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 15933615(E)-ethyl 3-(4-bromophenyl)-but-2-enoate

生成物 1

HCID 22557604(E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

Tetrakis(triphenylphoshine)palladium(0) (0.26 g, 0.22 mmol, 4 mol %) was added, under nitrogen, to a stirred solution of (E)-ethyl 3-(4-bromophenyl)-but-2-enoate (1.5 g, 5.57 mmol) {prepared as detailed in example 50 a} in DME (70 ml), and the resulting orange coloured solution stirred at room temperature for 10 min. Aqueous 2M sodium carbonate (16.7 ml, 33.4 mmol) was then added, the mixture stirred for 10 min, then 4-chlorophenyl boronic acid (1.3 g, 8.36 mmol) was added, and the reaction mixture heated to 80° C. for 18 h, under reflux. The reaction mixture was diluted with 1N HCl (100 ml) and the products extracted into ethyl acetate (2×100 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product, which was purified by column chromatography on silica gel (20% ethyl acetate in n-heptane eluent) to give the product, (E)-ethyl-3-(4′-chloro-biphenyl-4-yl)-but-2-enoate as a colourless solid; 1.17 g (70%).

後処理

  1. customprepared
  2. stirringthe mixture stirred for 10 min
  3. temperaturethe reaction mixture heated to 80° C. for 18 h
  4. temperatureunder reflux
  5. extractionthe products extracted into ethyl acetate (2×100 ml)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give the crude product, which
  10. customwas purified by column chromatography on silica gel (20% ethyl acetate in n-heptane eluent)

出典と根拠

ORDレコード
ord-e2e7ce1878b04af09efac478b6e6e93e
出典データセット
uspto-grants-2005_03
特許番号
US06867218B2

反応ノート

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