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T. He et al.
Letter
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(57) General Experimental Procedures for the Preparation of
Reduced Knoevenagel Adducts of Malononitrile
The mixture of aldehydes (0.2 mmol), malononitrile (0.24
mmol), and Hantzsch ester (0.24 mmol) in water (2.0 mL) was
stirred at 100 °C for 12 h. After the reaction mixtures were
cooled to room temperature, the crude solution was extracted
with EtOAc (3 × 3 mL). The combined organic layers were
washed with brine and dried over anhydrous Na2SO4. After
removal of solvents under reduced pressure, the residue was
purified through column chromatograph on silica gel to give the
pure products.
(58) General Experimental Procedures for the Preparation of
Reduced Knoevenagel Adducts of Ethyl 2-Cyanoacetate
The mixture of aldehydes (0.2 mmol), ethyl 2-cyanoacetate
(0.24 mmol), DEAE or K2CO3 (0.02 mmol), and Hantzsch ester
(0.24 mmol) in water (2.0 mL) was stirred at 100 °C for 12 h.
After the reaction mixtures were cooled to room temperature,
the crude solution was extracted with EtOAc (3 × 3 mL). The
combined organic layers were washed with brine and dried
over anhydrous Na2SO4. After removal of solvents under
reduced pressure, the residue was purified through column
chromatograph on silica gel to give the pure products.
(59) General Experimental Procedures the Preparation of
Reduced Knoevenagel Adducts of 2-(4-Nitrophenyl)-acetoni-
trile
The mixture of aldehydes (0.2 mmol), 2-(4-nitrophenyl)aceto-
nitrile (0.24 mmol), DEAE or K2CO3 (0.2 mmol), and Hantzsch
esters (0.24 mmol) in water (2.0 mL) was stirred at 100 °C for 12
h. After the reaction mixtures were cooled to room tempera-
ture, the crude solution was extracted with EtOAc (3 × 3 mL).
The combined organic layers were washed with brine and dried
over anhydrous Na2SO4. After removal of solvents under
reduced pressure, the residue was purified through column
chromatograph on silica gel to give the pure products.
(60) Gram-Scale Synthesis of 3-(Naphthalen-2-yl)-2-(4-nitrophe-
nyl)propanenitrile
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The mixture of 2-naphthaldehyde (1.00 g, 6.41 mmol), 2-(4-
nitrophenyl)acetonitrile (1.25 g, 7.69 mmol), DEAE (169.5 μL,
1.28 mmol), and Hantzsch ester (1.94 g, 7.69 mmol) in water
(10.0 mL) was stirred at 100 °C for 12 h. After the reaction mix-
tures were cooled to room temperature, the crude product was
separated by filtration. The pure product was obtained through
column chromatograph on silica gel.
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2016, 27, A–F