Реакция #155424

Уравнение реакции

4-morpholinecarbonyl chloride

3-fluoro-4-hydroxybenzaldehyde

CH2Cl2

pyridine

→

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

Выход 87.0%

Растворители

Water

Условия реакции

Обработка

1. 1
   ДругоеTo a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   Другоеat room temperature
4. 4
   Другоеovernight
5. 5
   ДругоеThe CH2Cl2 layer was separated
6. 6
   Экстракцияthe aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
7. 7
   СушкаThe combined CH2Cl2 solution was dried over Na2SO4
8. 8
   ДругоеAfter removal of the solvent
9. 9
   Другоеthe residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

Методика

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.

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