ChemicalBook CAS DataBase List 1-PHENYLCYCLOPENTENE

1-PHENYLCYCLOPENTENE synthesis

13synthesis methods

Product Name:1-PHENYLCYCLOPENTENE
CAS Number:825-54-7
Molecular formula:C11H12
Molecular Weight:144.21

120-92-3
399 suppliers
$11.00/25g

100-58-3
184 suppliers
$18.00/10ml

825-54-7
54 suppliers
$45.00/10mg

Yield: 100%

Reaction Conditions:

Stage #1:cyclopentanone;phenylmagnesium bromide in tetrahydrofuran;diethyl ether at 0;Reflux;
Stage #2: with hydrogenchloride in tetrahydrofuran;diethyl ether;water

Steps:

G.1
To a solution of 3.0 M solution of phenylmagnesium bromide in ether (49.7 mL, 149 mmol) was added TΗF (300 mL). To this solution cooled to 0⁰C cyclopentanone(13.23 mL, 149 mmol) was added. The reaction mixture was stirred at room temperature for 30 min, then - at reflux for 2 h. Ice (20 g) was added, followed by 6N HCl, until the precipitate dissolved. The product was extracted with ether. The combined etherial layers were washed with saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate and filtered. The solvent was removed in vacuum and the residue was purified by column chromatography on silica gel to give cyclopentenylbenzene (21.49 g, 149 mmol, 100 % yield) as colorless oil. LC-MS (M+H)⁺ = 145.1. ¹H NMR (500 MHz, CDCl₃) δ ppm 7.48 (2H, d, J=7.3 Hz), 7.35 (2H, t, J=7.8 Hz), 7.22 - 7.27 (IH, m), 6.22 (IH, t, J=2.1 Hz), 2.70 - 2.80 (2H, m), 2.52 - 2.64 (2H, m), 2.01 - 2.12 (2H, m).

References:

BRISTOL-MYERS SQUIBB COMPANY;BOY, Kenneth M.;GUERNON, Jason M.;MACOR, John E.;OLSON, Richard E.;SHI, Jianliang;THOMPSON, III, Lorin A.;WU, Yong-Jin;XU, Li;ZHANG, Yunhui;ZUEV, Dmitry S. WO2011/14535, 2011, A1 Location in patent:Page/Page column 50-51

930-29-0 Synthesis