Water → HCID 59643043, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(5-Bromo-2,3-dimethoxy-phenyl)-[1,3]dioxane (2 g, 6.6 mmol) in 13 mL dry THF cooled to −78° C., t-BuLi (1.5M solution in pentane, 2.5 eq.) was added dropwise via a syringe and the resulting dark red suspension was stirred 30 min. at −78° C. p-Tolualdehyde (1.2 g, 10 mmol, 1.5 eq.) was added dropwise to the mixture and the resulting clear solution was stirred 30 min at −78° C., then 30 min at 0° C. H2O (25 mL) was slowly added and the resulting solution was extracted with EtOAc (3×25 mL). The pooled organic fractions were dried over MgSO4 and evaporated in vacuo. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 3:2) to yield the desired compound as a colorless solid.

Provenance & Evidence