Triethyl phosphonoacetate → HCID 18349870, compound

Participants

Reaction Steps

7.30 ml of phosphonoacetic acid triethyl ester were dissolved in 100 ml of abs. THF. 3.90 g of KOtBu were added at 0° C. and the mixture stirred for 15 minutes at this temperature. 4.20 g of 1-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone, dissolved in 30 ml of THF, were added dropwise within 30 minutes at room temperature and stirring continued at 40° C. for 16 hours. The reaction mixture was then poured onto crashed ice/NH4Cl, extracted with EtOEt, washed with brine and H2O, and dried over Na2 SO4. Evaporation of the solvent, followed by flash chromatography (silica gel, hexane/AcOEt=97:3) yielded 3.70 g of (E)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-but-2-enoic acid ethyl ester as yellowish oil (GC-purity 98%).

Provenance & Evidence