Hydrochloric Acid → HCID 58593383, compound

Participants

Reaction Steps

To a solution of 2,6-di-tert-butyl-4-(1-{3,5-di-tert-butyl-4-[3-(2,2-dimethyl-[1,3]dioxo-lan-4(R)-yl)-propoxy]-phenylsulfanyl}-1-methyl-ethylsulfanyl)-phenol (Ex-11, 230 mg, 0.35 mmol) in 20 ml MeOH, was added 1.0 N HCl dropwise until the mixture turned cloudy. Then small amount of MeOH was added to the mixture until it became clear. The mixture was stirred at room temperature, and HPLC indicated that the reaction completed within 2 hours. The mixture was neutralized with 5N KOH and extracted with EtOAc. The combined organic phase was washed with water, dried over MgSO4, and concentrated to dryness. The residue was purified by silica gel column chromatography to give 0.2 g (93%) 5-{2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-pentane-1,2(S)-diol as a white solid, mp 68–71° C. 1H-NMR (CDCl3) δ 7.53 (s, 2H), 7.45 (s, 2H), 5.36(s, 1H), 3.67–3.79 (m, 4H), 3.46–3.52 (m, 1H), 1.91–2.17 (m, 4H), 1.42–1.45 (m, 42H). MS m/z: 636.4119 ([M+NH4]+, 20%). Anal. calcd for C36H58O4S2: C, 69.86; H, 9.44; S, 10.36; found: C, 70.10; H, 9.15, S, 10.13.

Provenance & Evidence