Tributyltin Chloride → 2-Methyl-5-(tributylstannyl)-1,3-thiazole

Participants

Reaction Steps

A −78° C. solution of 2-methylthiazole (2 g, 20.17 mmol) in THF (50 mL) was treated drop-wise with n-butyllithium (2.5 M in Hex, 10.49 mL, 26.2 mmol), stirred for 1 h, treated drop-wise with a solution of tributyltin chloride (7.11 mL, 26.2 mmol) in THF (25 mL) and stirred for an additional 1 h at −78° C. The mixture was allowed to warm to RT, stirred for 1 h, treated slowly with ice-cold satd. NaHCO3 (20 mL) and quickly extracted with Et2O (3×). The combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 2-methyl-5-(tributylstannyl)thiazole (6.67 g, 85%). 1H NMR (400 MHz, DMSO-d6): δ 7.55 (s, 1H), 2.67 (s, 3H), 1.54-1.45 (m, 6H), 1.30-1.23 (m, 6H), 1.09-1.04 (m, 6H), 0.83 (t, J=7.3 Hz, 9H).

Provenance & Evidence