Tetrahydrofuran → 6-(4-tert-Butoxycarbonylmethyl-phenylethynyl)-4,4,7-trimethyl-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid ethyl ester

4,4,7-Trimethyl-6-trimethylsilanylethynyl-1,2,3,4-tetrahydro-naphthalene-1-carboxylic acid ethyl ester (Intermediate 193, 0.26 g, 0.76 mmol) was treated with a 1M solution of tetra-n-butyl ammonium fluoride in tetrahydrofuran (3 mL, 3 mmol) under argon and the resulting reaction mixture was stirred at ambient temperature for 1 h. Water was added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered and evaporated to an oil that was used as such for the next step. Following General Procedure B and using the oil (0.76 mmol), 4-iodo-tert-butyl phenyl acetate (Reagent 10, 0.23 g, 0.72 mmol), triethyl amine (2 mL), copper(I)iodide (0.06 g, 0.32 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.14 g, 0.2 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 12% ethyl acetate in hexane as the eluent, the title compound was obtained as a viscous, pale yellow oil (0.23 g, 66%).

1. customthe resulting reaction mixture
2. extractionthe reaction mixture was extracted with diethyl ether
3. washThe organic phase was washed with water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated to an oil that

ORD-Eintrag

ord-ede1fc49493f4071ab53273c6a553417

Quelldatensatz

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07226951B2