反应详情

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, 1 H), 2.67 (s, 3 H), 1.54-1.45 (m, 6 H), 1.30-1.23 (m, 6 H), 1.09-1.04 (m, 6 H), 0.83 (t, J=7.3 Hz, 9 H).

1. stirringstirred for an additional 1 h at −78° C
2. stirringstirred for 1 h
3. additiontreated slowly with ice-cold satd
4. extractionNaHCO3 (20 mL) and quickly extracted with Et2O (3×)
5. washThe combined organics were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated to dryness
8. custompurified via silica gel chromatography (EtOAc/Hex)