반응 #155424

반응 방정식

4-morpholinecarbonyl chloride

3-fluoro-4-hydroxybenzaldehyde

CH2Cl2

pyridine

→

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

수율 87.0%

용매

Water

반응 조건

후처리

1. 1
   기타To a 250 mL dry round bottom flask
2. 2
   workup.STIRRINGThe mixture was stirred
3. 3
   기타at room temperature
4. 4
   기타overnight
5. 5
   기타The CH2Cl2 layer was separated
6. 6
   추출the aqueous layer was extracted continually with CH2Cl2 (50 mL×3)
7. 7
   건조The combined CH2Cl2 solution was dried over Na2SO4
8. 8
   기타After removal of the solvent
9. 9
   기타the residue was purified with a silica gel chromatography (heptane/ethyl acetate, gradient eluting)

실험 절차

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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