Trifluoroacetic acid → HCID 58046306, compound

Participants

Reaction Steps

To a solution of 4-((3,4-dichlorophenyl)(hydroxy)methyl)-3-methoxybenzamide (Preparation 156, 142 mg, 0.435 mmol) in DCM (5 mL) was added TFA (0.065 mL, 0.870 mmol) followed by triethylsilane (0.083 mL, 0.522 mmol) and the reaction stirred at room temperature for 72 hours. Further TFA (0.065 mL, 0.870 mmol) and triethylsilane (0.083 mL, 0.522 mmol) were added and the reaction stirred for a further 24 hours. The reaction was partitioned between saturated aq. NH4Cl (20 mL), and EtOAc (20 mL). The layers were separated and the aqueous was extracted with EtOAc (2×20 mL). The combined organics were washed with brine (20 mL), dried over MgSO4, filtered and the solvent removed in vacuo to give a white solid (165 mg, 100%). The material was used as crude in the next reaction without further purification.

Provenance & Evidence