Sodium Hydroxide → HCID 59199335, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,2-dimethyl-3-phenylsulfanyl-propionic acid (290 mg, 1.38 mmol) and Eaton's reagent (7 mL) is stirred for overnight at 65° C. The mixture is poured onto ice and basified by the addition of 1M aqueous NaOH. The mixture is extracted three times with dichloromethane. The combined extracts are dried with Na2SO4, filtered and concentrated. The resulting residue is then dissolved in ethanol (10 mL). The resulting solution is charged with NaBH4 (82.6 mg, 2.18 mmol). The mixture is stirred for 48 hours, quenched with 10% aqueous HCl, and concentrated to dryness. The resulting residue is purified by silica gel flash chromatography (ethyl acetate-heptane, 1:4) to afford (3,3-dimethyl-thiochroman-4-ol); 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (s, 3 H), 1.21 (s, 3 H), 1.58 (d, J=5.1 Hz, 1 H), 2.50 (d, J=13.4 Hz, 1 H), 3.26 (d, J=12.4 Hz, 1 H), 4.17 (d, J=4.6 Hz, 1 H), 6.99-7.09 (m, 1 H) 7.11-7.20 (m, 2 H), 7.27 (m, 1 H).

Provenance & Evidence