Water → 4-[(1-Tributylstannyl-2-naphthalenyl) methoxy]piperidine

Participants

Reaction Conditions

Reaction Steps

A solution of 1 (0.5 g, 1.6 mmole) in dry THF (50 ml) was cooled to -70° C. under argon. This was followed by the addition of 2.5 M solution of n-butylithiumin hexane (0.8 ml, 2.1 mmole) and tributyltin chloride (1.7 g, 5 mmole) and the reaction mixture was stirred for 30 min at -70° C. and then for 1 hr at room temperature. The rations mixture was then added to 50 ml of water and extracted with methylene chloride. The methylene chloride fractions were washed with saturated solution of NaHCO3, H2O, brine, dried with anhydrous MgSO4 and evaporated in vacuo to give 64 as light semi-solid. A single component was detected by TLC (ammonium hydroxide/methanol/ethyl acetate/hexane; 1:1:8:2) Rf, 0.5; NMR (CDCl3) d 0.8-1.5 (m, 27H, 3× n-butyl); d 4.6 (s, --CH--O-ring); d 7.8-8.0 (m, 6H, naphthyl).

Provenance & Evidence