ethyl (2R)-2-(2,4-dichlorophenoxy)propanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of KOH (2.48 g, 44.2 mmol, 15 eq) in H2O (12 mL) was added ethyl (R)-2-(2,4-dichlorophenoxy)propionate (compound 9a; 0.80 g, 3.05 mmol) in EtOH (12 mL) at room temperature. The solution was stirred for 4 hours, and then acidified with concentrated aqueous HCl (pH 3). The resulting solid was filtered, rinsed with water, and dried to yield a white powder which was used without further purification. The resulting solid was filtered rinsed with water dried to yield a white powder which was used without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2,4-dichlorophenol (compound 3; 3.0 g, 18.4 mmol), ethyl (S)-lactate (compound 8a; 2.39 g, 20.2 mmol, 1.1 eq), and triphenylphosphine (7.23 g, 27.6 mmol, 1.5 eq) in anhydrous THF (50 mL), diisopropylazodicarboxylate (5.46 g, 27.6 mmol, 1.5 eq) was added dropwise. The reaction mixture was stirred 16 hours at room temperature. The solvent was evaporated and the resulting residue was subjected to chromatography on silica gel with 2-5% EtOAc/hexanes. Product-containing fractions were pooled and evaporated to yield a pale yellow oil which was used without further purification: 1H NMR (CDCl3) δ 7.31 (d, 1H), 7.06 (dd, 1H), 6.75 (d, 1H), 4.70 (q, 1H), 4.21 (dq, 2H), 1.62 (d, 3H), 1.20 (t, 3H). The solvent was evaporated evaporated to yield a pale yellow oil which was used without further purification