Ethyl dichloroacetate → HCID 59447468, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(tert-butyldimethylsilyloxy)propanal (1 g, 5.31 mmol) and ethyl 2,2-dichloroacetate (0.651 mL, 5.31 mmol) in Et2O (4 mL) at 0° was dropwise added sodium ethanolate (0.397 g, 5.84 mmol) in EtOH (4 mL). The reaction mixture was stirred at 0° C. for 1.5 h and diluted with Et2O. The resulting mixture was washed with brine and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was dried in vacuo and dissolved in EtOH (8 mL). To the resulting solution was added Example 49A (1 eq) in DMF. The reaction mixture was heated at 50° C. for 8 hours and concentrated under reduced pressure. The residue was dissolved in DCM and purified by column chromatography on silica gel eluting with 0% to 17% EtOAc in hexanes, then with 0% to 15% EtOAc in DCM to provide the desired product 49B: LCMS (APCI): m/z 623 (M+H).

Provenance & Evidence