CID 406 → 4-Chloro-3-methoxy-1-(methoxy-5-chloro-tricyclo[3,3,1,13,7]dec-2-ylidenemethyl)-benzene

関与物質

反応条件

反応手順

Phosphonate 4 (3.2 g, 10 mmol) was dissolved in 30 ml dry THF under argon and cooled to -78° C. Dropwise addition of nBuLi (2.3M, 4.4 ml, 10.1 mmol) generated a yellow-orange phosphonate ylid. After stirring the ylid solution for 10 min, 5-chloro-2 adamantanone (1.75 g, 9.5 mmol), dissolved in 8 ml THF, was added dropwise to the ylid at -78° C. The reaction was slowly warmed to room temperature over 45 min and refluxed for 2 h. Upon cooling, the THF was stripped in vacuo and the product was partitioned between EtOAc/hexanes (1:1) and dilute NaHCO3. The organic layer was dried over NaHCO3. The organic layer was dried over Na2SO4, stripped of solvent and purified on silica gel (2-4% EtOAc/hexanes) to give 3.3 g (96%) of enol ether 5 as a colorless, viscous gum.

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