Water → Chloroform trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

5-azido-2-(2,2-dimethoxyethyl)-1,3-dioxane 40 (33.65 g, 155 mmol) was dissolved in CHCl3 (1 L) with water (6.25 mL, 347 mmol) and cooled to 0° C. TFA (250 mL, 3.366 mol) was added to the reaction mixture to give 20% TFA/CHCl3 which was stirred at 0° C. for 40 min. The reaction was quenched with solid NaHCO3 (400 g, 4.76 mol) at 0° C. The reaction mixture was filtered and concentrated. The resulting aldehyde was used in the next step without further purification.

Provenance & Evidence