Sodium hydride → 1-Methoxymethyl-4-tritylthio-2-azetidinone

Participants

Reaction Steps

A solution of 4-tritylthio-2-azetidinone (1.38 g, 4.0 mmoles) in THF (10 ml) was added to a well stirred suspension of sodium hydride (200 mg of commercial 50%, 4.1 mmoles, washed with pentane) in THF (10 ml) maintained at -15°. Methanol (12 drops) was added and the mixture was stirred at -15° for 0.5 h. Methoxymethyl bromide (0.58 g, 4.6 mmoles) was added and the mixture was stirred for 2h, diluted with ether, washed with water and brine, dried and concentrated to leave an oil (1.72 g). Crystallization from pentane gave a white solid (1.41 g) m.p. 72-76 δ (ppm, CDCl3): 7.3 (15H, m, aromatics), 4.4 (3H, m, NCH2O and H-4), 3.22 (3H, s, CH3), 2.76 (2H, m, H-3).

Provenance & Evidence