Lithium hydroxide, monohydrate → HCID 59268002, compound

Participants

Reaction Steps

To a solution of 2.17 g (6.18 mmol) of ethyl 2-methyl-2-{[(2S)-oxan-2-ylmethyl]sulfanyl}propanoate (70%) in THF/water (1/1, 40 mL) are added 1.39 g (18.52 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 2 d, then concentrated under reduced pressure to remove the organic solvent. The aqueous residue is washed with diethyl ether (200 mL), then acidified with 6N aqueous HCl solution and extracted with ethyl acetate (3×20 mL). The combined organic extracts are dried (MgSO4), filtered and the filtrate is concentrated under reduced pressure to give 2.07 g of 2-methyl-2-{[(2S)-oxan-2-ylmethyl]sulfanyl}propanoic acid (58 wt % by NMR, residual solvent). Yield: 89%, ES-MS: m/z 219 [M+H]; 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 1.29-1.42 (1 H, m), 1.45-1.61 (9 H, m), 1.65-1.73 (1 H, m), 1.80-1.90 (1 H, m), 2.71-2.75 (1 H, m), 2.78-2.84 (1 H, m), 3.37-3.49 (2 H, m), 4.00 (1 H, dt, J=11.41, 2.16 Hz).

Provenance & Evidence