Lithium Hydroxide → HCID 14358757, compound

Participants

Reaction Steps

To a solution of (R)-(+)-Methyl 2-(tert-butyldimethylsilyloxy)propanoate (5.26 g, 24.09 mmol) in THF (283 mL) at 0° C. was added an aqueous LiOH solution (0.2 M, 283 mL). After stirring at room temperature for 4 hr, the reaction mixture was concentrated to 50% of the original volume and extracted with petroleum ether (2×50 mL). The ether extracts were combined and extracted with a saturated aqueous NaHCO3 solution (50 mL). The aqueous layers were combined and acidified to pH 3 to 4 with an aqueous KHSO4 solution (1M, 100 mL). The aqueous solution was extracted with petroleum ether (3×250 mL) and the combined organic layers were dried over Na2SO4 and concentrated to afford 5.45 g of (R)-(+)-2-(tert-butyldimethylsilyloxy)propanoic acid as colorless oil (100%, product contains ˜10% water). 1H NMR (CDCl3): δ 4.29 (q, 1H, J=6.8 Hz, —CH), 1.38 (d, 3H, J=6.8 Hz, —CH3), 0.86 (s, 9H, Si—(CH3)3), 0.07 (s, 3H, Si—CH3), 0.06 (s, 3H, Si—CH3).

Provenance & Evidence