Formaldehyde → Tributyl[(methoxymethoxy)methyl]stannane

Participants

Reaction Conditions

Reaction Steps

n-BuLi (9.96 mmol, 6.2 mL, 1.6M) was added dropwise to a -78° C. solution of diisopropylamine (1.4 mL, 9.96 mmol) in dry THF (20 mL). The solution was stirred for 10 min. at 0° C., then tributyltinhydride (9.96 mmol, 2.68 mL) was added and the solution stirred for 15 min. The solution was cannulated into a 0° C. solution of paraformaldehyde (9.96 mmol, 0.3 g) and the solution stirred at rt for 3 hours. The reaction was quenched with NH4Cl and extracted with pentane (4x), dried (MgSO4), and concentrated. The crude material was dissolved in CH2Cl2 (40 mL), dimethylaniline (14.9 mmol, 1.9 mL) was added and the solution cooled to 0° C. Chloromethylmethylether (14.9 mmol, 1.13 mL) was added and the reaction stirred for 2 hours. The reaction was diluted with pentane and then washed with cold 0.5M HCl, water, saturated NaHCO3 and dried (Na2SO4). Flash chromatography (25% CH2Cl2 /hexane) affords 1.49 g (41%) of (methoxymethoxymethyl)tributyl tin.

Provenance & Evidence