1-Indanone → 1-Phenyl-1H-indene

HRID 361948노트

반응식

HRID 361948 반응식
C1(=O)C2C(=CC=CC=2)CC1.C1([Mg]Br)C=CC=CC=1.[C:19]1([C:25]2(O)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)C>[C:19]1([CH:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=[CH:26]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 67351-IndanoneHCID 122547581-Phenyl-1-indanolHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 5196741-Phenyl-1H-indene수율 95.9%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

1-Indanone (13.30 g, 0.1006 moles) was stirred in diethylether (300 mL) at -78° C. as PhMgBr (0.150 moles, 50.00 mL of 3.0M solution in diethylether) was added. The mixture was then allowed to slowly warm to 20°-25° C. and then stirred 16 hours. After the reaction period the mixture was poured on ice and then extracted with aqueous solutions of 1M HCI (1×100 mL), 1M NaHCO3 (1×100 mL), andthen H2O (1×100 mL). The organic layer was then dried over MgSO4. Filtration followed by removal of the volatiles resulted in the isolation of a yellow oil which by NMR was seen to still contain some 1-phenyl-1-indanol. This oil was then distilled under vacuum to yield the desired product as a pale yellow oil (18.56 g, 95.9 percent).

후처리

  1. additionwas added
  2. temperatureto slowly warm to 20°-25° C.
  3. customAfter the reaction period the mixture
  4. additionwas poured on ice
  5. extractionextracted with aqueous solutions of 1M HCI (1×100 mL), 1M NaHCO3 (1×100 mL), andthen H2O (1×100 mL)
  6. dry with materialThe organic layer was then dried over MgSO4
  7. filtrationFiltration
  8. customfollowed by removal of the volatiles
  9. customresulted in the isolation of a yellow oil which by NMR
  10. distillationThis oil was then distilled under vacuum

출처 및 근거

ORD 기록
ord-b31589cc69694298b5602cf2d3cb8cc0
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866704

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