3-Bromopropionaldehyde dimethylacetal → HCID 18329867, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from Step D (317 mg, 0.850 mmol) in 2.0 mL of tetrahydrofuran at −78° C. was added lithium hexamethyldisilazide solution dropwise (1.02 mL, 1.02 mmol, 1.0 M in THF). After 45 minutes, 3-bromopropionaldehyde dimethyl acetal was added (0.231 mL, 1.70 mmol). The reaction was warmed to 0° C. and stirred for 2 hours, then poured into EtOAc/sat. NaHCO3 solution. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by silica gel column chromatography (3-5% MeOH/CH2Cl2) to provide the desired product as a 1:1.5 mixture with the starting material.

Provenance & Evidence