Chloroacetaldehyde → HCID 59178949, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the product of Example 12.24, Step 1 above (151 mg; 0.374 mmol) in DMF (3 ml) was treated with Ac2O (1 ml) and chloroacetaldehyde (587 mg; 50% aq. solution; 3.74 mmol). The solution was stirred at 80° C. for 1 hr. The reaction was partitioned between iPrOAc (50 mL) and aq. sodium bicarbonate (20 mL). The organic was washed three more times with aq. sodium bicarbonate (3×10 mL). The organic was dried over magnesium sulfate, filtered and evaporated to a brown semi-solid. The solid was digested (refluxing MTBE). The nearly homogenous solution was allowed to stand at −10° C. for 1 hr, causing the deposition of a tan solid. The supernatant was drawn off and the solid rinsed with MTBE. All volatiles were removed and light tan solid was chromatographed (PTLC; 40:1 CH2Cl2/MeOH), affording the title compound.

Provenance & Evidence