P-Chloroacetophenone → 1-[4-[(E)-2-phenylethenyl]phenyl]ethanone

HRID 13897

反応式

HRID 13897 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(C(N)C2CCCCC2)CCCCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC([B-](C2C=CC(C)=CC=2)(C2C=CC(C)=CC=2)C2C=CC(C)=CC=2)=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.O1CCCC1>[C:8]([C:5]1[CH:6]=[CH:7][C:2](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

参加物

7

反応物 3

HCID 7467P-ChloroacetophenoneHCID 7501StyreneHCID 10774245alpha-Cyclohexylcyclohexanemethanamine

生成物 1

HCID 15174621-[4-[(E)-2-phenylethenyl]phenyl]ethanone収率 75.7%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 23136639Tri-tert-butylphosphonium tetra-para-tolylborate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.773 g (5 mmol) of 4′-chloroacetophenone, 1.042 g (10 mmol) of styrene, 0.034 g (0.038 mmol) of tris(dibenzylideneacetone)dipalladium (0), 1.074 g (5.5 mmol) of dicyclohexylmethylamine and 5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.087 g (0.15 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 37 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.841 g of (trans)-4-acetylstilbene (yield: 75 mol % based on 4′-chloroacetophenone). The identification of the product was made by mass spectroscopy, 1H-NMR and 13C-NMR.

後処理

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 30° C. for 37 hours
  5. customAfter the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
  6. additionwere added
  7. customfollowed by separation
  8. customThe organic phase was purified by column chromatography

出典と根拠

ORDレコード
ord-19258c922369402ea534cdd954c7fc1d
出典データセット
uspto-grants-2010_06
特許番号
US07728176B2

関連ノート

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