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

HRID 1736477

Reaction equation

[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

Participants

Conditions

Temperature: 40 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-0bbff7524b774ea89cdb78632010a69b
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05541217

Linked notes

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