Synthesis
GENERAL METHOD: 5 mL of a 0.24 M solution of diorganometallic reagent 1b or 1c (1.2 mmol) was cooled to 0 °C and appropriate arylacetic acid 2 (1.1 mmol) dissolved in 5 mL of anhydrous THF was added. The resulting mixture was stirred vigorously at 0°C for 2 hours. To the cooled dark brown mixture at the same temperature, 1.7 mmol of appropriate electrophilic reagent was added. The reaction mixture was stirred vigorously and allowed to warm slowly to room temperature overnight. Upon completion of the reaction, the reaction was quenched by slow dropwise addition of 15 mL of H2O. The organic solvent was evaporated in vacuum and the residue was extracted with CH2Cl2 (3 × 10 mL). The aqueous phase was acidified with 1N HCl and extracted again with CH2Cl2 (3 × 10 mL). The organic phases were combined, washed sequentially with H2O (1 × 10 mL) and brine (10 mL), dried (Na2SO4), and the solvent evaporated. The crude product was purified and characterized as follows. For the reaction mixture containing crude β-hydroxyacid 2df, 15 mL of 10% HCl (containing about 15 g of crushed ice) was added on quenching and post-treated as described above. After solvent evaporation, the crude product was purified and characterized as follows. Quenching with D2O was performed in the same manner as the above procedure.
References
[1] Organic Syntheses, 2017, vol. 94, p. 1 - 15
[2] Tetrahedron, 2011, vol. 67, # 19, p. 3470 - 3475
[3] Bulletin de la Societe Chimique de France, 1965, p. 1881 - 1888
[4] Journal of the American Chemical Society, 2011, vol. 133, # 31, p. 11936 - 11939
