Formaldehyde → Tributyl[(methoxymethoxy)methyl]stannane

Temperature

0 °C

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.

1. stirringthe solution stirred for 15 min
2. customwas cannulated into a 0° C.
3. stirringthe solution stirred at rt for 3 hours
4. customThe reaction was quenched with NH4Cl
5. extractionextracted with pentane (4x)
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. dissolutionThe crude material was dissolved in CH2Cl2 (40 mL)
9. temperaturethe solution cooled to 0° C
10. stirringthe reaction stirred for 2 hours
11. washwashed with cold 0.5M HCl, water, saturated NaHCO3
12. dry with materialdried (Na2SO4)

ORD record

ord-5282ece944ca408584f5acc81ee93b95

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05519040