1,2-Bis(diphenylphosphino)ethane → (Cyclopent-2-en-1-yl)benzene

HRID 1736477

반응식

HRID 1736477 반응식
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:13]1[CH2:17][CH2:16][CH:15]=[CH:14]1)(=O)C.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.[Cl-].[Zn+2].[Cl-].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.[Pd]>[C:1]1([CH:17]2[CH2:16][CH2:15][CH:14]=[CH:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

7

반응물 3

HCID 742671,2-Bis(diphenylphosphino)ethaneHCID 140735Acetic acid, cyclopent-2-en-1-yl esterHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 142190(Cyclopent-2-en-1-yl)benzene

시약·촉매·용매 3

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium촉매HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
40 °C

실험 절차

A solution of 8 mL of 2M phenylmagnesium bromide in THF was added dropwise to a solution of 32.2 mL (0.016 mole) of 0.5M zinc chloride in THF. A solution of 3.05g (0.024 mole) of 3-acetoxycyclopent-1-ene in 25 mL of dry THF was added, and 321 mg of 1,2-bis(diphenylphosphino)ethane and 462 mg of palladium bis(dibenzylideneacetone) added. The reaction mixture was heated at 40° C. for 18h. The reaction was cooled to room temperature and the solids filtered off. Ether was added, and the organic layer was washed sequentially with saturated ammonium chloride, water, and brine. After drying (MgSO4), the solvent was evaporated in vacuo to give 6 g of a yellow oil. Flash chromatography (SiO2) eluting with hexane gave 760 mg of an oil. Mass spectrum (Cl-NH3) m/z=145 (M+1); 300 MHz NMR (CDCl3) δ 1.68-1.78 (m, 1H); 2.32-2.6 (m, 3H); 3.85-3.96 (m, 1H); 5.72-5.82 (m, 1H); 5.92-6.01 (m, 1H); 7.12-7.38 (m, 5H).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationthe solids filtered off
  3. additionEther was added
  4. washthe organic layer was washed sequentially with saturated ammonium chloride, water, and brine
  5. dry with materialAfter drying (MgSO4)
  6. customthe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-0bbff7524b774ea89cdb78632010a69b
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541217

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