Water → HCID 59548936, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Tin (II) chloride dihydrate (18.238 g, 81.00 mmol) in EtOH (65.00 mL) and HCl (12 M, 10.00 mL) was stirred at 70° C. until the solution became clear. Compound 21 (5.60 g, 20.28 mmol) was then added over 10 min. The solution was kept slightly refluxing during addition. The reaction was monitored with TCL (25% EtOAc in hexanes, Rf=0.65). The reaction was complete after refluxing for 1.5 hrs, as indicated by the absence of the starting material (TLC). Water (80 mL) was added and the resulting solution was allowed to cool to room temperature. The desired product was precipitated out as a white solid during cooling. The mixture was further cooled and stirred for 30 min at 15° C. The resulting precipitation was collected via filtration under vacuum, washed with water, and dried under vacuum to yield compound 22 as a white solid (3.60 g, 99.0% HPLC purity, 63% yield). 1H NMR (500 MHz, DMSO-d6): δ 7.44 (m, 1H), 7.09 (m, 2H), 7.04 (m, 1H), 6.92 (dd, J1=2 Hz, J2=8 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 5.65 (s, 2H).

Provenance & Evidence