Yield:50262-49-2 100%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 0 - 20;Inert atmosphere;

Steps:

Representative procedure for the preparation of intermediates 2a - i.

General procedure: 4-formylphenyl propionate (2b) is used as an example. To a solution of 4-hydroxybenzaldehyde (1) (1.0 g, 8.19 mmol) in THF (25 mL) at 0 oC was added Et₃N (1.71 mL, 12.2 mmol) followed by propionyl chloride (1.06 mL, 12.2 mmol). The reaction mixture was warmed to room temperature and stirred for 3 h. At this point, the reaction mixture was diluted with EtOAc and quenched with aqueous NH₄Cl. The aqueous layer was extracted with EtOAc (2) and the combined organic layers were subsequently washed with H₂O and brine, and concentrated in vacuo. The resulting residue was purified by column chromatography (hexanes/EtOAc, 3:1) to provide compound 2b as a colorless oil.

References:

Zakhari, Joseph S.;Kinoyama, Isao;Hixon, Mark S.;Di Mola, Antonia;Globisch, Daniel;Janda, Kim D. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 21,p. 6203 - 6209] Location in patent:supporting information; experimental part