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Freshly distilled methyl acetate (8.6 mL, 0.11 mol) was added.
After 1 h, ethanolamine (7.49 ml, 0.125 mol) was added dropwise to the reaction solution.
1-Bromooctane (8.7 mL, 0.05 mol) was added dropwise through a drop funnel.
To this solution 5 (6.3 kg, 10.25 mol) was added under vigorous stirring.
After stirring for 15 min, NaOH (13.9 g, 0.35 mol) was added at room temperature.
To this mixture, 4 mL of pyridine (0.05 mol) was added and shaken well for 2 hours.
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To a solution of an aldehyde (1 mole) and 5,5-dimethyl-1,3-cyclohexanedione 5,5-dimethyl-1,3-cyclohexanedione 5,5-dimethyl-1,3-cyclohexanedione 5,5-dimethyl-1,3-cyclohexanedione
Platinum (0.5 mol%) was added to the manganese oxide (10 mol%) catalyst to improve its activity.
First-generation Grubbs' catalyst (15 mol %) was added to a degassed solution of the corresponding Ugi product (1 equiv) in CH2Cl2 (ca. 0.06 mol L−1) at 45 °C.
Then DBSNa (20 mol%) was added and the reaction mixture was stirred at room temperature for the desired time as monitored by TLC (Table 1).
To a stirred mixture of 2-aminobenzophenone (2 mmol) and acetylenic ester (2 mmol) in EtOAc, 5 ml SnO2 nanoparticles (5 mol%) was added.
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