Reacción #1566443

Ecuación de reacción

diisopropyl azodicarboxylate

2-tert-butyl-4-chloro-5-hydroxy-2H-pyridazin-3-one

product

{4-[2-(tert-butyldimethylsilanyloxy)ethoxymethyl]phenyl}methanol

triphenylphosphine

→

oil

Rendimiento 66.7%

2-tert-butyl-4-chloro-5-{4-[2-(tert-butyldimethylsilanyloxy)ethoxymethyl]benzyloxy}-2H-pyridazin-3-one

Rendimiento 66.7%

Disolventes

ethyl acetate

hexane

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroconsumption of the pyridazinone starting material
2. 2
   Concentraciónthe reaction was concentrated in vacuo
3. 3
   OtroThe crude material was purified by flash column chromatography (90:10 pentane:ethyl acetate)

Procedimiento

To a solution of 2-tert-butyl-4-chloro-5-hydroxy-2H-pyridazin-3-one (212 mg, 1.047 mmol) in THF (15 mL) was added the product of Example 8C (475 mg, 1.570 mmol), triphenylphosphine (412 mg, 1.570 mmol), and then diisopropyl azodicarboxylate (DIAD, 304 μL, 1.570 mmol). The reaction was stirred at room temperature for 2 hours under nitrogen atmosphere. Thin layer chromatography (1:1 hexane:ethyl acetate) indicated consumption of the pyridazinone starting material and the reaction was concentrated in vacuo. The crude material was purified by flash column chromatography (90:10 pentane:ethyl acetate) to obtain a clear oil (336 mg, 66% yield). 1H NMR (600 MHz, CDCl3): 7.70 (s, 1H), 7.39 (m, 4H), 4.58 (s, 2H), 1.63 (s, 9H), 0.90 (s, 9H), 0.07 (s, 6H); HRMS calcd for C24H31D6ClN2O4Si: 509.24738, found 509.2480.

Fuente