Tributyltin Chloride → HCID 23658640, compound

Participants

Reaction Steps

2.00 g (14.5 mmol) of 3-methoxybenzyl alcohol were dissolved in 40 ml of dry benzene. At 0° C., 19.91 ml (31.9 mmol, 2.2 eq.) of a 1.6 molar n-BuLi solution were slowly added dropwise, where the white suspension formed after addition of one equivalent of n-BuLi changed its color to dark red during the addition of the second equivalent. Stirring at RT was continued for another 2 hours, and 5.1 ml (18.8 mmol, 1.3 eq.) of tributyltin chloride were then added at 0° C. The mixture was stirred at RT overnight, and 40 ml of saturated NH4Cl solution were then added and the mixture was extracted three times with 70 ml of EA. After washing of the organic phase with saturated NaCl solution and drying over MgSO4, the solvent was removed. The crude product was purified by column chromatography (reversed-phase silica RP-18, MeCN), which gave 4.83 g (11.3 mmol, 78%) of 3-methoxy-2-(tributylstannyl)benzyl alcohol as a colorless oil. In a further experiment, a yield of 60% was obtained.

Provenance & Evidence