Chlorotrimethylsilane → HCID 59637594, compound

Participants

Reaction Conditions

Reaction Steps

4,6,7-Trimethoxy-8-methyl-2-naphthoic acid (1) (0.276 g, 1 mmol) is added at −78° C. to a mixture containing the base LTMP (4.2 mmol) and TMSCl (0.998 mL, 5.7 mmol) in anhydrous THF (10 mL). The reaction mixture is stirred at −78° C. for 1 h then gradually heated to ambient temperature over 3 h. After hydrolysis, the reaction mixture is treated with a solution of 2M NaOH (pH 10). The aqueous phase is washed with ethyl ether (2×15 mL), acidified with 2M HCl (pH 1-2) then extracted with dichloromethane (3×20 mL). The combined organic phases are dried over MgSO4, filtered, then concentrated under reduced pressure. The residue is purified by recrystallization (cyclohexane/ethyl acetate) to give 4,6,7-trimethoxy-8-((trimethylsilyl)methyl)-2-naphthoic acid (2) (0.307 g, 88%). 1H NMR (200 MHz, CDCl3): 8.37 (s, 1H), 7.44 (s, 1H), 7.40 (s, 1H), 4.07 (s, 3H, OCH3), 4.03 (s, 3H, OCH3), 3.88 (s, 3H, OCH3), 2.63 (s, 2H, CH2), 0.02 (s, 9H, Si(CH3)3). SMHR, [M+H]+ calculated for C18H25O5Si: 349.1471. Found: 349.1468.

Provenance & Evidence