Water → 4-Phenyl-5-methylindene

HRID 1257556노트

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HRID 1257556 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][CH2:21]2.O>COCCOC.C1C=CC([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)=CC=1>[C:1]1([C:17]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][CH2:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 58444066HCID 58444066, 화합물

생성물 1

HCID 231155034-Phenyl-5-methylindene수율 86%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

phenylboronic acid (8.3 g, 68 mmol) was dissolved in ethylene glycol dimethylether (DME, 100 mL), and aqueous solution (100 mL) of cesium carbonate (30 g), 4-bromo-5-methylindene (10 g, 48 mmol), tetrakis(triphenylphosphine)palladium (3.0 g, 2.6 mmol) were sequentially added. Solution was reacted for 55 hours while heating under reflux, then, reaction solution was added into water (200 mL), and extracted with diisopropylether. Organic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride, then was dried over sodium sulfate, and solvent was distilled off under reduced pressure to obtain the crude product. This was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane) to obtain 4-phenyl-5-methylindene (8.5 g, yield: 86%) as colorless liquid.

후처리

  1. customSolution was reacted for 55 hours
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customreaction solution
  5. extractionextracted with diisopropylether
  6. washOrganic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride
  7. dry with materialwas dried over sodium sulfate, and solvent
  8. distillationwas distilled off under reduced pressure
  9. customto obtain the crude product
  10. customThis was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane)

출처 및 근거

ORD 기록
ord-839bbbff49434a55959b0998cef7ae6d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461365B2

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