Triethylamine → HCID 23498918, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1 g (3 mmol) of 2-bromo-3-methyl-6-acetoxy -5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene, 0.68 ml (4.42 mmol) of trimethoxyvinyl silane, 0.12 g (0.53 mmol), 0.36 g of Tri-o-tolylphosphine (1.2 mmol) and 0.82 mL of triethylamine (5.9 mmol) in 10 mL of N-methyl pyrollidine was heated at 90° C. After 3 hours, the reaction was cooled to room temperature and 0.57 mL (3.5 mmol) of ethyl4-bromobenzoate, 0.82 mL of triethylamine (5.9 mmol) and 5 mL (5 mmol) of tetrabutylammonium fluoride were added. The reaction mixture was heated to 90° again. After 2.5 hours, the reaction was cooled to room temperature, poured into brine and extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution 2-5% ethyl acetate/hexane) to afford 0.2 g (20%) of Ethyl-4-[(E)-2-(5,5,8,8-Tetramethyl-3-methyl-6-acetoxy-5,6,7,8-tetrahydro-naphthalen-2-yl)vinyl]benzoate (M+=434).

Provenance & Evidence