Cesium carbonate → HCID 86657858、化合物

HRID 1257561ノート

反応式

HRID 1257561 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][C:21]1[C:22](Br)=[C:23]2[C:27](=[CH:28][CH:29]=1)[CH2:26][CH:25]=[CH:24]2>C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:22]1[C:21]([CH3:20])=[CH:29][CH:28]=[C:27]2[C:23]=1[CH:24]=[CH:25][CH2:26]2

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 58444066HCID 58444066、化合物

生成物 1

HCID 86657858HCID 86657858、化合物収率 74%

試薬・触媒・溶媒 2

HCID 178420554HCID 178420554、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To mixed solution of 2-naphthylboronic acid (5 g, 29 mmol) and DME (100 mL), aqueous solution (30 mL) of cesium carbonate (12 g, 36.8 mmol)(30 mL) and 5-methyl-4-bromoindene (4.3 g, 21 mmol), tetrakis(triphenylphosphino)palladium (0.9 g) were added, and heated under reflux. After 16 hours, reaction solution was poured into 1N HCl-ice water to separate organic layer after stirring. Organic layer was washed with saturated solution of sodium chloride after filtering through Celite, and dried over magnesium sulfate, and solvent was distilled off under reduced pressure. The obtained crude product was purified by column chromatography (Silica-gel: produced by Kanto Chemical Co., Inc., hexane) to obtain the desired 4-(2-naphthyl)-5-methylindene (3.9 g, yield: 74%).

後処理

  1. additionwere added
  2. temperatureheated
  3. temperatureunder reflux
  4. customreaction solution
  5. customto separate organic layer
  6. washOrganic layer was washed with saturated solution of sodium chloride
  7. filtrationafter filtering through Celite
  8. dry with materialdried over magnesium sulfate, and solvent
  9. distillationwas distilled off under reduced pressure
  10. customThe obtained crude product
  11. customwas purified by column chromatography (Silica-gel: produced by Kanto Chemical Co., Inc., hexane)

出典と根拠

ORDレコード
ord-2fd3eb1ec7bc418cbe2aaf31d2e0e766
出典データセット
uspto-grants-2013_06
特許番号
US08461365B2

反応ノート

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