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

HRID 1736477

反応式

HRID 1736477 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladium触媒HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0bbff7524b774ea89cdb78632010a69b
出典データセット
uspto-grants-1996_07
特許番号
US05541217

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