Acetic Acid → 1310419-07-8

Participants

Reaction Conditions

Reaction Steps

To a cooled (−25° C.) solution of 5-iodo-3-methylisothiazole (59.5 g, 264 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (50.2 g, 270 mmol) in anhydrous THF (300 mL) was added dropwise 1.3 M isopropylmagnesium lithium chloride in THF (218 mL, 283 mmol) at a rate which maintained the temperature at −15° C. to −25° C. The reaction mixture was stirred at −10° C. for 5 minutes after the addition was completed. HPLC analysis indicated that the starting material was consumed. A solution of acetic acid (16.19 mL, 283 mmol) in THF (40 mL) was added slowly to the reaction solution at 0° C. Hexanes (250 mL) and MTBE (150 mL) were sequentially added to the reaction mixture. A solid precipitate was formed, which was filtered off by passing the reaction mixture through a pad of Celite. The filtrate was concentrated via rotary evaporation to afford an oil residue, which was dispersed in MTBE (500 mL) through vigorous stirring. Additional precipitate was formed, which was filtered off using a pad of Celite. The filtrate was again concentrated to an oil, and MTBE (200 mL) was added, which formed additional solid precipitate that was filtered off using a pad of Celite. The process was repeated two more times until no more solid was formed when MTBE was added to the oil residue. The oil was dried in a rotary evaporator under high vacuum overnight with a bath temperature of 20° C., which afforded the title compound as an oil (49.55 g, 83%). 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (s, 12H), 2.56 (s, 3H), 7.41 (s, 1H).

Provenance & Evidence