Diisopropylamine → HCID 69460947, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of i-Pr2NH (0.921 mL, 1.2 eq) in anh. THF (22 mL), at 0° C., under N2, was added a 1.6 M solution of BuLi in hexane (3.42 mL, 1 eq) and the mixture was stirred at 0° C. for 10 min. It was then cooled to −78° C. and a solution of methyl 2,4-dichlorophenylacetate (1.2 g, 5.478 mmol) in anh. THF (3.3 mL) was added dropwise. The mixture was stirred at −78° C. for 45 min before the addition of a solution of ethyl 4-iodobutyrate (1.72 g, 1.3 eq) in anh. THF (2 mL). The cooling bath was then removed and the mixture was stirred at r.t. for 4 hr. The solvents were evaporated under reduced pressure. The residue was dissolved in CH2Cl2, washed with water (2×25 mL) and brine (1×25 mL) and dried over anh. Na2SO4. The solids were filtered and the solvent evaporated. The crude product was purified by flash chromatography (silica gel, cHex/EtOAc 9:1). Mixed fractions were repurified with the same eluent. The title compound was obtained as a pale yellow oil (1.36 g, 4.088 mmol, 75%).

Provenance & Evidence