Michael U. Luescher, Chalupat Jindakun, J. Bode
Nov 10, 2018
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Journal
Organic Syntheses
Abstract
A. Tributyl(chloromethyl)stannane (1). An oven-dried 500-mL pear-shaped recovery flask equipped with a 34 x 16 mm, Teflon-coated, oval magnetic stir bar is charged with anhydrous THF (150 mL) (Note 2) and N,Ndiisopropylamine (10.6 mL, 7.65 g, 75.6 mmol, 1.1 equiv) (Note 3) via a syringe. The flask is fitted with a rubber septum and a nitrogen inlet needle, after which the stir rate is set to ca. 375 rpm (Figure 1A). The reaction is cooled to 0–5 °C using an ice/water bath before the dropwise addition of nBuLi (47.8 mL, 75.6 mmol, 1.1 equiv) (Note 4) via a 20 mL syringe over 25 min (Figure 1B). The resulting clear pale-yellow solution is stirred further at 0–5 °C for 30 min before tributyltin hydride (18.5 mL, 20.0 g, 68.7 mmol, 1.0 equiv) (Note 5) is added dropwise via syringe over 15 min (Figure 1C). The resulting clear yellow solution is stirred further at 0–5 °C for 30 min before paraformaldehyde (2.30 g, 76.6 mmol, 1.1 equiv) (Note 6) is weighed under air into a glass vial and charged in one portion to the reaction flask. Bu3Sn Cl Bu3SnH DIPA, n-BuLi, (CH2)nO, THF; then CH3SO2Cl