Compound 20

Tributyl(iodomethyl)stannane

From: SnAP reagents for the one-step synthesis of medium-ring saturated N-heterocycles from aldehydes

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InChIKey XEKIDGIZQAEOKB-UHFFFAOYSA-N

Synonyms:
  • Tributylstannyliodomethane,
  • Tributyl(iodomethyl)stannane

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound 20 was prepared according to a modified literature procedure (Seitz, D. E., Carroll, J. J., Cartaya M., C. P., Lee, S.-H. & Zapata, A. Efficient synthesis of derivatives of tributylstannylmethanol. Synthetic Communications 13, 129–134 (1983)): To a stirred solution of the chloride 19 (54.9 g, 162 mmol, 1.00 equiv) in acetone (800 mL) at rt was added sodium iodide (49.7 g, 332 mmol, 2.05 equiv) in one portion. The resulting suspension was stirred at rt for 16 h. The reaction mixture was concentrated to give a colorless suspension that was filtered through a short plug of silica (hexanes rinse). The filtrate was concentrated to afford pure iodide 20 (68.6 g, 98% yield) as clear, colorless liquid. 1NMR (400 MHz, CDCl3): δ 1.95 (s, J(117/119Sn-1H) = 17.8 Hz, 2H) 1.62-1.44 (m, 6H), 1.33 (sext, J = 7.2 Hz, 6H), 1.08-0.95 (m, 6H), 0.91 (t, J = 7.2 Hz, 9H); 13C NMR (100 MHz, CDCl3): δ 29.0, 27.4, 13.8, 10.8.

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