Tris(1,1-dimethylethyl)phosphine → 8,9-Dihydrocyclopenta[def]phenanthrene

HRID 505846

반응식

HRID 505846 반응식
Br[C:2]1[CH:15]=[C:14]2[CH2:16][C:11]3[C:12]4[C:13]2=[C:4]([CH2:5][CH2:6][C:7]=4[CH:8]=[C:9](Br)[CH:10]=3)[CH:3]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:3]1[C:4]2[CH2:5][CH2:6][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[CH2:16][C:14]([C:13]=2[C:12]=34)=[CH:15][CH:2]=1

참가 물질

6

반응물 3

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 125243672,6-dibromo-8,9-dihydro-4H-cyclopenta[def]phenanthreneHCID 23676156Sodium t-butoxide

생성물 1

HCID 6057498,9-Dihydrocyclopenta[def]phenanthrene

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

실험 절차

The compound 2 (0.65 g, 1.747 mmol), bis(4-biphenyl)amine (TCI Corp.) (1.40 g, 4.37 mmol), sodium tert-butoxide (0.51 g, 0.5 mmol), Pd2(dba)3 [(tris(dibenzylidene acetone) dipalladium(0))] (0.08 g, 0.087 mmol), and tri(tert-butyl)phosphine (0.017 g, 0.087 mmol) in a 50 ml round bottom flask were dissolved with toluene (10 mL), and the reaction mixture was refluxed for 12 hours. After the reaction was terminated, the reaction solution was cooled to room temperature and extracted with distilled water (100 ml). The combined organic layers were dried over MgSO4, concentrated, and purified by silica gel column chromatography. The eluate was concentrated and dried to give a material 1 represented by Formula 9 (1.1 g, yield: 75%).

후처리

  1. temperaturethe reaction mixture was refluxed for 12 hours
  2. customAfter the reaction was terminated
  3. extractionextracted with distilled water (100 ml)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography
  7. concentrationThe eluate was concentrated
  8. customdried

출처 및 근거

ORD 기록
ord-8b7c8c2324154b9ca43810a032ea800f
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781579B2

연결된 노트

불러오는 중…