Ammonium Chloride → 3-(3-Carbomethoxyphenyl)methyl-4,6-dihydroxy-chroman

Participants

Reaction Steps

To a solution of the product of Step 3 (700 mg, 2.4 mmol) in 5 ml MeOH and 1 ml THF at r.t. was added NaBH4 (80 mg, 2.4 mmol). The solution was stirred at r.t. for 0.5 hr. The mixture was poured into cold NH4Cl solution, extracted with HOAc, and chromatographed on silica gel (eluted with 40% EtOAc/hexane) to give 441 mg (58%) of the cis isomer and 279 mg (37%) of the trans isomer of the title compound.

Provenance & Evidence