Sodium Hydroxide → HCID 22983872, compound

Participants

Reaction Steps

To a refluxing solution of compound 94 (506 mg, 1.35 mmol) in acetone (120 mL), H2O (24 mL) and aqueous 1 M NaOH (24 mL, 24.0 mmol) was portionwise added with care solid Na2S2O4 (3.89 g, 18.97 mmol). The reflux was continued for 2 h then the acetone was removed under vacuum. More H2O (50 mL) was added and the aqueous phase was extracted with CH2Cl2 (4×). The organic phase was dried (MgSO4), filtered then rotary evaporated. The crude solid was purified by flash chromatography (SiO2) using 3:7 to 1:1 EtOAc/Hexanes as eluent to give compound 95 (228 mg, 49%) as a foamy solid. 1H NMR (CDCl3) δ 0.88 (3H, s), 1.37-2.78 (14H, m), 3.41 (3H, s), 3.71 (2H, t, J=5.0 Hz), 4.09 (2H, 2.9 Hz), 6.52 (1H, s), 6.65 (1H, s).

Provenance & Evidence