Sodium Thiosulfate → HCID 86627924, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(3-bromophenyl)-but-2-en-1-ol (1.03 g, 4.54 mmol) in DCM (10 mL) at 0 deg C., was added Dess-Martin periodinane (2.11 g, 5 mmol). The resulting suspension was warmed to 23° C. and stirred for approx. 30 min. until the reaction was complete by TLC. The mixture was poured into 50 mL of saturated aqueous NaHCO3, containing Na2S2O3 (1 g). This mixture was stirred vigorously until both layers became clear. The aqueous layer was extracted with DCM (2×) and the combined organic layers were dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by flash chromatography (10% EtOAc/hexanes) to afford the titled compound as a white solid (910 mg, 89% yield) that was a 5:1 ratio of E:Z isomers.

Provenance & Evidence