Acetic acid, azido-, ethyl ester → Methyl alpha-azido-4-[bis(tert-butoxy)phosphorylhydroxymethyl]cinnamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 6.45 g (50 mmol) of ethyl α-azidoacetate and 1.64 g (5.0 mmol) of 4-[bis(tert-butoxy) -phosphorylhydroxymethyl)benzaldehyde 6 in MeOH (20 mL) at -78° C. was added a total of 7.4 mL (40 mmol) of NaOMe, 5.4M in MeOH, dropwise over 5 minutes. The mixture was stirred 5 minutes at -78° C. then an additional 1 hour at 0° C. The resulting light yellow suspension was subjected to an extractive work up (brine/EtOAc) to yield a light yellow crystalline solid, which was triturated with CHCl3 /pet. ether (35°-60° C.) to yield 7 as light yellow crystals, 1.26 g (57%), mp 111°-113° C.

Provenance & Evidence