Cesium carbonate → HCID 86657858, 화합물

HRID 1257561노트

반응식

HRID 1257561 반응식
[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

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 2734375(Naphthalen-2-yl)boronic acidHCID 58444066HCID 58444066, 화합물

생성물 1

HCID 86657858HCID 86657858, 화합물수율 74%

시약·촉매·용매 2

HCID 178420554HCID 178420554, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-2fd3eb1ec7bc418cbe2aaf31d2e0e766
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461365B2

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