Sodium hydride → HCID 54525740, compound

Participants

Reaction Steps

A solution of dimethyl 4-methylsulfonylbenzylphosphonate prepared as described in Ulman et al U.S. Pat. No. 4,792,208 (6.29 g, 22.6 mmol), 60% sodium hydride dispersion (1.35 g, 33.9 mmol) and 50 mL of dry 1,2-dimethoxyethane (DME) under nitrogen was treated with a solution of 4-[(2-acetoxyethyl)methylamino]benzaldehyde (5.00 g, 22.6 mmol, Example 5) in 50 mL of DME. The resulting mixture was heated at reflux for 16 hr, then cooled and poured onto 300 g of ice. The resulting yellow solid was filtered, washed with water and air-dried. The solid was heated at reflux in a mixture of 10 g of NaOH, 90 mL of ethanol and 90 mL of water for 24 hr, then cooled and poured onto 200 mL of water. The resulting brown solid was filtered and air-dried. The product was recrystallized twice from a mixture of ethanol and pyridine to produce 4.46 g (60%) of yellow plates, m.p. 201°-204° C.

Provenance & Evidence