| 98% |
With sulfuric acid at 20 - 75℃; for 12h; |
1.1. General methods for propiolic acids (A1-A8)
To a solution of cinnamic acid (0.96 g, 6.48 mmol) in methanol (50 mL) at room temperature was added concentrated sulfuric acid (0.50 mL). The resulting solution was allowed to stir at 75 °C. The reaction was monitored by TLC. After reaction completed, the solution was diluted with water (200 mL) and the aqueous layer was extracted with dichloromethane (4×50 mL). The combined organic layer was washed with saturated NaHCO3 solution and then washed with water. The solvent was dried over anhydrous Na2SO4, filtered, and concentrated in vacuum to afford methyl cinnamate (1.03 g, 98%). |
| 97% |
With dodeca-tungstophosphoric acid for 4h; Reflux; |
|
| 97% |
With sulfuric acid at 100℃; for 12h; Sealed tube; Molecular sieve; Further stages; |
|
| 96% |
With thionyl chloride for 4h; Reflux; |
|
| 94% |
With silicium tetrachloride for 5h; Heating; |
|
| 93.07% |
With N-benzyl-N,N,N-trimethyl-ammonium chloride; toluene-4-sulfonic acid at 76℃; for 3h; |
1-5
Weigh 7.41g (0.05mol) cinnamic acid and 4.81g (0.15mol) methanol, put them into a three-necked flask, stir and heat to 76°C,Then add 3.66g (30%) catalyst BTAC-PTSA to the three-necked flask and perform heating and reflux reaction at this temperature, the reaction time is 3h; after the reaction is over, the reaction liquid is hot and divided into two phases of water and oil through a separatory funnel , The water phase is vacuum dried at 50°C to recover the catalyst; the oil phase is poured into a beaker while it is hot and the beaker is placed in a 45°C water bath, and an appropriate amount of 4% sodium carbonate solution is added under constant stirring until it is weakly alkaline ( pH=7~8), stand for layering, remove the water phase; add three times the volume of 5 deionized water to the oil phase under constant stirring to precipitate crystals, then suction filter and wash with deionized water until the filtrate is neutral. White or light yellow solid, after drying, the target product methyl cinnamate is obtained, and the yield is 93.07% |
| 87% |
With 1,3-diazabicyclo[5.4.0]-undec-7-ene; 5-hydro-3-oxaoctafluoropentanesulfonyl fluoride In dichloromethane at 20℃; for 37h; |
|
| 82% |
With 1,3,5-trichloro-2,4,6-triazine; anhydrous sodium carbonate at 50℃; for 0.166667h; Sonication; |
General Procedure
General procedure: The carboxylic acid (0.271 mmol), TCT (0.050 g, 0.271 mmol), PS-Ph3P (0.009 g, 0.027 mmol, loading 3.0 mmol/g), and Na2CO3 (0.057 g, 0.542 mmol) were added to MeOH (0.5 mL). Then the mixture was sonicated in an ultrasonic bath (Elmasonic S 30H) at 50°C for the specified time. After completion, the crude mixture was filtered through a short pad of silica to obtain the product after solvent evaporation. Whenever necessary, the product was further purified by flash chromatography. |
| 82% |
With sulfuric acid for 4h; Reflux; |
|
| 79% |
Stage #1: Cinnamic acid With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 0.0833333h;
Stage #2: methanol In dichloromethane at 20℃; |
|
| 78% |
With diphosphorus pentoxide Heating; |
|
| 78% |
for 15h; Heating; |
|
| 73% |
With bismuth trifluoromethanesulphonate for 5.5h; Reflux; |
|
| 71% |
With sulfuric acid for 24h; Reflux; |
General procedure for the synthesis of compounds 9-12 and 21-29
General procedure: After dissolving the carboxylic acid in the alcohol, three drops of H2SO4 95% were added to the solution and the mixture was refluxed for 24 h. The solvent was evaporated under reduced pressure and water was added to the crude mixture. The pH of the aqueous layer was adjusted to 7 adding drops of a saturated solution of NaHCO3 and brine was added in the mixture. The aqueous layer was extracted three times with ethyl acetate; the organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure yielding the final compound. Further purification step was made when it was necessary. |
| 70% |
With oxygen; potassium carbonate In hexane at 20℃; for 14h; Sonication; |
|
| 68% |
With iron(III) perchlorate for 3h; Ambient temperature; |
|
| 68.5% |
With sulfuric acid for 4h; Heating; |
|
| 67.2% |
Stage #1: Cinnamic acid With thionyl chloride In 1,4-dioxane at 0℃; for 0.5h;
Stage #2: methanol In 1,4-dioxane at 25℃; for 12h; |
The first step: the preparation of methyl cinnamate
The cinnamic acid (1.62g, 10mmol)After dissolving in dioxane (30 mL),Under stirring at 0 °C, thionyl chloride (3.54 g, 30 mmol) was added in portions,After 30 minutes, methanol (0.48 g, 15 mmol) andA mixture of dioxane (10 mL),After the addition was complete, the mixture was stirred at 25°C for 12 hours.The solvent was evaporated under reduced pressure with a rotary evaporator.1.09 g of colorless oil was obtained, yield: 67.2%. |
| 54% |
With beef pancreas lipase at 20℃; for 12h; |
|
| 20% |
With nickel (II) chloride for 14.5h; Heating; |
|
|
With sulfuric acid for 5h; Heating; |
|
|
With toluene-4-sulfonic acid Reflux; |
|
|
With sulfuric acid for 12h; Reflux; |
|
|
With sulfuric acid Reflux; |
|
|
With sulfuric acid |
|
|
With hydrogenchloride at 20℃; |
|
|
With hydrogenchloride In lithium hydroxide monohydrate for 8h; Reflux; |
|
|
With sulfuric acid for 16h; Reflux; |
|
|
With thionyl chloride at 0 - 80℃; |
|
|
With sulfuric acid |
|
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