Reaktion #482103

Reaktionsgleichung

triethylsilane

oxo-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester

butoxytrimethylsilane

hydrochloric acid

trimethylsilyl triflate

→

title product

Ausbeute 56.8%

(RS)-butoxy-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic Acid Ethyl Ester

Ausbeute 56.8%

Lösungsmittel

water

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 26 hours
2. 2
   Extraktionextracted with ether
3. 3
   WaschenThe organic phase was washed with water
4. 4
   Trocknendried (Na2SO4)
5. 5
   Sonstigethe solvent evaporated
6. 6
   SonstigeThe oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane)

Vorschrift

6 g of oxo-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester and 2.6 g of butoxytrimethylsilane were dissolved in 200 ml of methylene chloride. The solution was cooled to 0° C., treated with 400 mg of trimethylsilyl triflate and stirred at 0° C. for 1.5 hours. After the dropwise addition of 2 g of triethylsilane, the reaction mixture was stirred at room temperature for 26 hours, then diluted with 500 ml of water, acidified with 2N hydrochloric acid and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated. The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane) to give 3.5 g of the title product as colorless oil.

Quelle