Water → HCID 24974098, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyltriphenylphosphonium iodide (12 g, 30 mmol) in THF (200 mL) was added dropwise n-BuLi (18.5 mL, 30 mmol) at 0° C. The suspension was stirred at 0° C. until a yellow color persisted, and then cyclopentadecanone, 48, (2.21 g, 9.8 mmol) was added as a solution in THF (20 mL). The mixture was allowed to warm to room temperature and stirred overnight. Upon completion, H2O was added to quench any remaining n-BuLi and any precipitates were filtered off. The filtrate was concentrated in vacuo and the residue was redissolved in CH2Cl2, washed three times with deionized H2O. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and then concentrated under reduced pressure to give a pale red oil. After column chromatography (Rf=0.9, 10% CH2Cl2/90% hexanes) 51 was isolated as a pale yellow oil (1.5 g, 69%). 1H NMR (CDCl3) δ 4.65 (s, 2H), 1.96 (t, 4H), 1.37 (m, 4H), 1.27-1.25 (m, 20H).48

Provenance & Evidence