Hydrochloric Acid → Sec-Butylbenzene

(1R,7S)-1,3,10,10-Tetramethyltricyclo-[5.2.1 .02,6 ]-deca-2,5-dienyl)(η5 -cyclopentadienyl)titanium dichloride (21 mg, 0.05 mmol, prepared as in Example 6) together with 2-phenyl-1-butene (132 mg, 1 mmol) and freshly distilled toluene (5 ml) were placed into a 50 ml round-bottomed flask. After degassing with three freeze/thaw cycles the vessel was filled with hydrogen (3 evacuate/refill cycles). n-Butyllithium (0.2 ml, 22.5 M, 0.5 mmol) was then added via syringe at room temperature and the resulting dark grey/green reaction mixture was stirred under a pressure of 20 p.s.i. hydrogen, while excluding light, for 40 hours. The hydrogen pressure was vented and the reaction vessel opened to air. Aqueous hydrochloric acid (2 ml, 5 M) was added and mixture was stirred for 5 minutes. The organic phase was separated and the aqueous phase extracted with ether (3×5 ml). The combined organic phases were dried (sodium sulphate) and the solvents removed iii vacuo to provide 2-phenylbutane (56 mg, 0.42 mmol) of 10.3% ee (assessed using gas chromatography, Astec α-DA column, 65° C.).

1. customAfter degassing with three freeze/thaw cycles the vessel
2. additionwas filled with hydrogen (3 evacuate/refill cycles)
3. customThe organic phase was separated
4. extractionthe aqueous phase extracted with ether (3×5 ml)
5. dry with materialThe combined organic phases were dried (sodium sulphate)
6. customthe solvents removed iii vacuo

ORD-Eintrag

ord-11d64296e4c2474b8b19a06bbc3bc0d9

Quelldatensatz

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05929266