Reacción #155424

Ecuación de reacción

4-morpholinecarbonyl chloride

3-fluoro-4-hydroxybenzaldehyde

CH2Cl2

pyridine

→

2-fluoro-4-formylphenyl morpholine-4-carboxylate

Rendimiento 87.0%

Disolventes

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   Otroat room temperature
4. 4
   Otroovernight
5. 5
   OtroThe CH2Cl2 layer was separated
6. 6
   Extracciónthe aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
7. 7
   SecadoThe combined CH2Cl2 solution was dried over Na2SO4
8. 8
   OtroAfter removal of the solvent
9. 9
   Otrothe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

Procedimiento

To a 250 mL dry round bottom flask were added 3-fluoro-4-hydroxybenzaldehyde (4.76 g, 34.0 mmol), anhydrous CH2Cl2 (40 mL) and pyridine (3.6 mL, 44.2 mmol). The mixture was stirred in an ice-water bath, then 4-morpholinecarbonyl chloride (4.4 mL, 37.4 mmol) was added. The mixture was stirred and warmed slowly to room temperature, then at room temperature overnight. Water (80 mL) was added to the reaction mixture. The CH2Cl2 layer was separated, and the aqueous layer was extracted continually with CH2Cl2 (50 mL×3). The combined CH2Cl2 solution was dried over Na2SO4. After removal of the solvent, the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting) to give 2-fluoro-4-formylphenyl morpholine-4-carboxylate (7.45 g) as white solid. Yield: 87%. 1H NMR (CDCl3, 300 MHz): δ=9.97 (s, 1H), 7.74-7.70 (m, 2H), 7.45 (t, J=7.8 Hz, 1H), 3.81-3.61 (m, 8H). 13C NMR (CDCl3, 75.5 MHz, mixture of two isomers): δ=189.9, 156.5, 153.1, 151.8, 144.0, 143.8, 135.0, 134.9, 126.7, 126.6, 124.8, 116.7, 116.4, 66.4, 66.3, 45.2, 44.4.

Fuente