Tributyltin Chloride → HCID 57634076, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL flame-dried 3-neck round-bottomed flask was added tert-butyl 4-(methoxymethyl)thiazol-2-ylcarbamate (1.75 g, 7.2 mmol) and 200 mL of dry THF. The resulting solution was stirred at −78° C. and treated dropwise with 1.6 M n-BuLi in THF (9.4 mL, 15 mmol) over 15 minutes. The resulting pale yellow solution was stirred at −78° C. for 30 minutes and was then treated dropwise with tributyltin chloride (2.1 mL, 7.9 mmol). The reaction mixture was stirred at −78° C. for 30 minutes. The bath was then removed, and the mixture was allowed to warm to room temperature and was stirred at room temperature for 2.5 hours. The reaction was quenched by the addition of saturated NH4Cl (150 mL). The layers were separated, and the aqueous layer was washed with Et2O (3×100 mL). The organic phases were combined and washed with NaCl (100 mL) dried over MgSO4, filtered, and concentrated in vacuo to provide the crude produce as a viscous oil which was then purified by column chromatography using a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 10% to 20% EtOAc in hexane, to provide tert-butyl 4-(methoxymethyl)-5-(tributylstannyl)thiazol-2-ylcarbamate (2.5 g, 65% yield) as waxy oil. MS m/z: 535 (M+1).

Provenance & Evidence