Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of triethyl 2-phosphonopropionate (47 g, 0.19 mol) in THF (200 mL) was added solid magnesium bromide etherate (59 g, 0.23 mol) under nitrogen. Triethylamine (26.5 mL, 0.19 mol) was added after 5 min. The mixture was stirred for 10 min and 4-(methylthio)benzaldehyde (27.1 mL, 0.19 mol) was added. After 15 h at room temperature the mixture was diluted with water (400 mL) and hexane (400 mL). The two layers were separated. The organic layer was washed with water (400 mL), dried over 4 Å molecular sieves, filtered, and concentrated to give 42.5 g (95%) of ester 6a as a light yellow oil: IR (neat) 2980, 1705, and 1240 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 7.63 (1 H), 7.33 (2 H), 7.25 (2 H), 4.26 (2 H), 2.50 (3 H), 2.12 (3 H), and 1.34 (3 H); 13C NMR (CDCl3, 75.5 MHz) δ 168.71, 139.37, 138.08, 132.55, 130.19, 127.98, 125.89, 60.87, 15.38, 14.37 and 14.17.
The two layers were separated
The organic layer was washed with water (400 mL)
dried over 4 Å molecular sieves
filtered
concentrated
Source ID: ord-11c045263ed64978a107e051f15eea11