Name: 2386-25-6|3-Acetyl-2,4-dimethylpyrrole|98%
Brand: Ambeed
SKU: A460827
Price: 25.0 USD
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1
[ 2199-63-5 ]
[ 2386-25-6 ]
1-[5-(2,5-dimethyl-pyrrol-3-ylmethylene)-2,4-dimethyl-5H-pyrrol-3-yl]-ethanone [ No CAS ]

Reference： [1]Piloty; Krannich; Will [Chemische Berichte, 1914, vol. 47, p. 2541]

2
[ 2386-25-6 ]
[ 776-24-9 ]
4-[bis-(4-acetyl-3,5-dimethyl-pyrrol-2-yl)-methyl]-2,5-dimethyl-pyrrole-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium pyrosulfate

Reference： [1]Fischer; Heyse [Justus Liebigs Annalen der Chemie, 1924, vol. 439, p. 251]

3
[ 2386-25-6 ]
[ 2386-35-8 ]
[ 2524-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol

Reference： [1]Schlesinger et al. [Journal of the American Chemical Society, 1950, vol. 72, p. 2867,2871]

4
[ 2386-25-6 ]
[ 517-22-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With lithium aluminium tetrahydride
75%	With lithium aluminium tetrahydride In tetrahydrofuran for 4.5h; Heating;
60%	With lithium aluminium tetrahydride In tetrahydrofuran at 85℃; for 4h;	2.3 Example 2 Synthesis of compound 8 Step:3 Compound 7 (8.20g, 60mmol) was dissolved in anhydrous tetrahydrofuran, and the mixture was added dropwise to an aluminum hydrideLithium (4.54 g) in tetrahydrofuran, and the mixture was refluxed at 85 ° C for 4 h. TLC was monitored until the reaction was complete. The unreacted lithium aluminum hydride was quenched by the addition of ethyl acetate, ethanol and water in the order of ice bath. Extracted with dichloromethane, extracted three times with dichloromethane, and the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, and dried. The eluant was petroleum ether: ethyl acetate = 10: 1. The product was a reddish-brown liquid with light aroma, and the yield was about 60%.

	With lithium aluminium tetrahydride; diethyl ether
	With hydrazine hydrate Erhitzen des erhaltenen Hydrazons mit Natriumaethylat-Loesung im Rohr auf 150-160grad;
	With sodium ethanolate; hydrazine hydrate at 175 - 190℃; unter Druck;
	With lithium aluminium tetrahydride In tetrahydrofuran for 5h; Cooling with ice; Reflux;

Reference： [1]Location in patent: body text Murat-Onana, Marie Laure; Berini, Christophe; Minassian, Frederic; Pelloux-Leon, Nadia; Denis, Jean-Noel [Organic and Biomolecular Chemistry, 2010, vol. 8, # 9, p. 2204 - 2211]
[2]Mula, Soumyaditya; Ray, Alok K.; Banerjee, Manas; Chaudhuri, Tandrima; Dasgupta, Kamalesh; Chattopadhyay, Subrata [Journal of Organic Chemistry, 2008, vol. 73, # 6, p. 2146 - 2154]
[3]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN103626793, 2016, B Location in patent: Paragraph 0020; 0057; 0060
[4]Treibs; Scherer [Justus Liebigs Annalen der Chemie, 1952, vol. 577, p. 139,146]
[5]Willstaetter; Asahina [Chemische Berichte, 1911, vol. 44, p. 3709] Knorr; Hess [Chemische Berichte, 1911, vol. 44, p. 2763][Chemische Berichte, 1912, vol. 45, p. 2626 Anm. 1]
[6]Fischer; Ammann [Chemische Berichte, 1923, vol. 56, p. 2320,2328]
[7]Chen, Ji-An; Gao, Jie; Gu, Xianfeng; Li, Mimi; Tan, Jiahui; Yin, Xiaofan; Zhao, Zhen [Organic and biomolecular chemistry, 2020, vol. 18, # 25, p. 4744 - 4747]

5
[ 2386-25-6 ]
[ 1500-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	at 300℃;
	at 300℃;

Reference： [1]Colacicchi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1912, vol. <5>21, p. I 657]
[2]Colacicchi [Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1912, vol. <5>21, p. I 657]

6
[ 2386-25-6 ]
[ 202286-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; acetic acid
	With N-Bromosuccinimide; sodium sulfite In tetrahydrofuran; water	45 3-Acetyl-5-bromo-2,4-dimethyl-1H-pyrrole (Step 1) 3-Acetyl-5-bromo-2,4-dimethyl-1H-pyrrole (Step 1) To a stirred suspension of 3-acetyl-2,4-dimethyl-1H-pyrrole (2.89 g, 21.1 mmol) in THF (80 mL) was added NBS (3.75 g, 21.1 mmol) at -78° C. under nitrogen. After stirring for 30 minutes at same temperature, the mixture was allowed to warm to room temperature and stirred for 1 hour. Sodium sulfite (4.3 g) was added to the mixture and volatiles were removed by evaporation. Water (100 mL) was added to the mixture, and the precipitates were collected by filtration to give 5.33 g (quant. including water) of the subtitle product. 1H-NMR (CDCl3) δ 8.08 (br. s, 1H), 2.49 (s, 3H), 2.42 (s, 3H), 2.22 (s, 3H).
1.8 g	With N-Bromosuccinimide In tetrahydrofuran at -78℃; for 1h;	General procedure A for the synthesis of compounds 6a - 6g General procedure: To a stirred ice-cooled solution of compound 1a - 1e (20mmol) in HOAc (40mL), the sodium nitrite (30mmol) in H2O (5mL) was added dropwise. The reaction mixture was stirred at r.t. for about 3h, then Zn (40mmol) and pentane-2,4-dione (20mmol) was added at 0°C. And the reaction mixture was heated to 85°C for about 4h. Upon completion, the reaction mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. The residue was chromatographed, eluting with a gradient of 2-10% EtOAc/petroleum ether to afford compound 2a - 2e (yield, 58-89%) as a clear oil. (0047) To a suspension of compound 2a - 2e (10mmol), KOH (50mmol) in ethylene glycol (20mL). The resulting mixture was stirred at 140°C for about 3h. After completion of reaction, the mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum to give 3a - 3e (yield, 72-91%) without further purification. (0048) To a solution of 3a (2.0g, 14.6mmol) in THF (20mL) at - 78°C was added NBS (2.6g, 14.6mmol) in four batches. The reaction mixture was stirred at - 78°C for 1h. Then the reaction was partitioned between water and ethyl acetate, the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed, eluting with a gradient of 10-20% EtOAc/petroleum ether to afford compound 4 (1.8g, yield, 57%) as a yellow solid. (0049) A mixture of 3a - 3e (10mmol) in anhydrous DMF (20mL) was stirred at 0°C, the solution was added dropwise POCl3 (20mmol). The mixture was stirred at ambient temperature for about 3h. Then the mixture was added dropwise 5M KOAc (50mmol) solution at 0°C, and the solution was stirred at 105°C under nitrogen for about 3h. After cooling, the mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting crude product was purified by silica gel column chromatography (10-30% EtOAc/petroleum ether) to yield 5a - 5e (yield, 51-74%) as a brown solid. (0050) A flask was charged with compound 4 (0.22g, 1mmol), corresponding boric ester (1.2mmol), PdCl2(dppf) (0.1mmol), K2CO3 (5mmol) and sparged with nitrogen. Degassed dioxane (7mL) and water (2mL) was added and the mixture was heated at 100°C for 4h. The reaction mixture was partitioned between water and ethyl acetate, the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography (30-80% EtOAc/petroleum ether) to yield 6a - 6e (yield, 49-68%) as a white solid. (0051) A mixture of 5a (0.2g, 1.2mmol), Na2S2O5 (0.023g, 0.12mmol), benzene-1,2-diamine (0.13g, 1.2mmol) or 2-aminobenzenethiol (0.15g, 1.2mmol) in DMF (10mL) was degassed under a stream of nitrogen. The resulting brown solution was heated at 140°C overnight. The cooled reaction was purified by silica gel column chromatography (gradient elution, 1-2% MeOH/dichloromethane) to afford 6f - 6g (yield, 59, 62%) as a white solid.

Reference： [1]Fischer,H.; Bartholomaeus [Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1913, vol. 87, p. 261]
[2]Current Patent Assignee: PFIZER INC - US2002/49235, 2002, A1
[3]Bian, Yuanyuan; Chen, Yadong; Hong, Qianqian; Jiang, Fei; Kong, Bo; Li, Hongmei; Lu, Tao; Ma, Yu; Ran, Ting; Tang, Weifang; Wang, Cong; Yang, Na; Zhang, Zhimin; Zheng, Wan; Zhu, Jiapeng; Zhu, Zhaohong [European Journal of Medicinal Chemistry, 2022, vol. 227]

7
[ 2386-25-6 ]
[ 861035-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium; toluene und Behandeln der Reaktionsloesung mit Chlorokohlensaeure-aethylester;

Reference： [1]Rainey; Adkins [Journal of the American Chemical Society, 1939, vol. 61, p. 1104,1105]

8
[ 2386-25-6 ]
[ 5666-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-dioxane; nickel at 190℃; Hydrogenation; isomer(ic) II;
	Multi-step reaction with 2 steps 1: hydrazine hydrate / Erhitzen des erhaltenen Hydrazons mit Natriumaethylat-Loesung im Rohr auf 150-160grad 2: hydriodic acid; red phosphorus / 240 °C / anschliessend Hydrierung in Aether in Gegenwart von Platinmohr bei 20grad

Reference： [1]Moffett; White [Journal of Organic Chemistry, 1952, vol. 17, p. 407,412]
[2]Willstaetter; Asahina [Chemische Berichte, 1911, vol. 44, p. 3709]

9
[ 2386-26-7 ]
[ 2386-25-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide In ethylene glycol at 160℃; for 4h;
96%	With potassium hydroxide In ethylene glycol at 160℃; for 4h;	2.2 Step 2: Synthesis of compound 7: Compound 6 (20.00 g, 9.60 mmol) was placed in a round bottom flask and ethylene glycol (80.00 ml) was added followed by potassium hydroxide (10. 00 g) To 160 ° C reflux reaction 4h. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and dried to give a brown red solid in a yield of about 96%.
86%	With potassium hydroxide In 1,2-dimethoxyethane at 160℃; for 4h;

	With sodium hydroxide; ethanol und Erhitzen der erhaltenen Saeure in Glycerin;
	With potassium hydroxide In ethylene glycol at 140℃; for 3h;	General procedure A for the synthesis of compounds 6a - 6g General procedure: To a stirred ice-cooled solution of compound 1a - 1e (20mmol) in HOAc (40mL), the sodium nitrite (30mmol) in H2O (5mL) was added dropwise. The reaction mixture was stirred at r.t. for about 3h, then Zn (40mmol) and pentane-2,4-dione (20mmol) was added at 0°C. And the reaction mixture was heated to 85°C for about 4h. Upon completion, the reaction mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum. The residue was chromatographed, eluting with a gradient of 2-10% EtOAc/petroleum ether to afford compound 2a - 2e (yield, 58-89%) as a clear oil. (0047) To a suspension of compound 2a - 2e (10mmol), KOH (50mmol) in ethylene glycol (20mL). The resulting mixture was stirred at 140°C for about 3h. After completion of reaction, the mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum to give 3a - 3e (yield, 72-91%) without further purification. (0048) To a solution of 3a (2.0g, 14.6mmol) in THF (20mL) at - 78°C was added NBS (2.6g, 14.6mmol) in four batches. The reaction mixture was stirred at - 78°C for 1h. Then the reaction was partitioned between water and ethyl acetate, the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers was washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed, eluting with a gradient of 10-20% EtOAc/petroleum ether to afford compound 4 (1.8g, yield, 57%) as a yellow solid. (0049) A mixture of 3a - 3e (10mmol) in anhydrous DMF (20mL) was stirred at 0°C, the solution was added dropwise POCl3 (20mmol). The mixture was stirred at ambient temperature for about 3h. Then the mixture was added dropwise 5M KOAc (50mmol) solution at 0°C, and the solution was stirred at 105°C under nitrogen for about 3h. After cooling, the mixture was poured into water and was extracted with ethyl acetate (100mL×3). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting crude product was purified by silica gel column chromatography (10-30% EtOAc/petroleum ether) to yield 5a - 5e (yield, 51-74%) as a brown solid. (0050) A flask was charged with compound 4 (0.22g, 1mmol), corresponding boric ester (1.2mmol), PdCl2(dppf) (0.1mmol), K2CO3 (5mmol) and sparged with nitrogen. Degassed dioxane (7mL) and water (2mL) was added and the mixture was heated at 100°C for 4h. The reaction mixture was partitioned between water and ethyl acetate, the aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography (30-80% EtOAc/petroleum ether) to yield 6a - 6e (yield, 49-68%) as a white solid. (0051) A mixture of 5a (0.2g, 1.2mmol), Na2S2O5 (0.023g, 0.12mmol), benzene-1,2-diamine (0.13g, 1.2mmol) or 2-aminobenzenethiol (0.15g, 1.2mmol) in DMF (10mL) was degassed under a stream of nitrogen. The resulting brown solution was heated at 140°C overnight. The cooled reaction was purified by silica gel column chromatography (gradient elution, 1-2% MeOH/dichloromethane) to afford 6f - 6g (yield, 59, 62%) as a white solid.

Reference： [1]Mula, Soumyaditya; Ray, Alok K.; Banerjee, Manas; Chaudhuri, Tandrima; Dasgupta, Kamalesh; Chattopadhyay, Subrata [Journal of Organic Chemistry, 2008, vol. 73, # 6, p. 2146 - 2154]
[2]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN103626793, 2016, B Location in patent: Paragraph 0020; 0057; 0059
[3]Chen, Ji-An; Gao, Jie; Gu, Xianfeng; Li, Mimi; Tan, Jiahui; Yin, Xiaofan; Zhao, Zhen [Organic and biomolecular chemistry, 2020, vol. 18, # 25, p. 4744 - 4747]
[4]Rainey; Adkins [Journal of the American Chemical Society, 1939, vol. 61, p. 1104,1105]
[5]Bian, Yuanyuan; Chen, Yadong; Hong, Qianqian; Jiang, Fei; Kong, Bo; Li, Hongmei; Lu, Tao; Ma, Yu; Ran, Ting; Tang, Weifang; Wang, Cong; Yang, Na; Zhang, Zhimin; Zheng, Wan; Zhu, Jiapeng; Zhu, Zhaohong [European Journal of Medicinal Chemistry, 2022, vol. 227]

10
[ 2386-27-8 ]
[ 2386-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; nickel at 110 - 120℃; Hydrogenation;

Reference： [1]Johnson et al. [Journal of the Chemical Society, 1958, p. 4254][Org. Synth. Coll. Vol. V. <1973> 1022]

11
[ 2386-25-6 ]
[ 66154-85-6 ]
[ 69818-70-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid at 100℃; for 2h;

Reference： [1]Clezy, Peter S.; Phuc, Le van; Prashar, Jognandan K. [Australian Journal of Chemistry, 1991, vol. 44, # 8, p. 1061 - 1075]

12
[ 2386-25-6 ]
[ 78-94-4 ]
[ 78956-76-0 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride In ethanol for 1h; Heating;

Reference： [1]Treibs, Alfred; Wilhelm, Roland; Hermann, Erwin [Liebigs Annalen der Chemie, 1981, # 5, p. 849 - 857]

13
[ 2386-25-6 ]
[ 148526-13-0 ]
dibenzyl 3,3'bis<2-(methoxycarbonyl)ethyl>-4,3',5'-trimethyl-2,2'(1,1'-(15)N)dipyrrolmethane-5,5'-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid In water at 90℃; for 1h;

Reference： [1]Schlabach, Martin; Limbach, Hans-Heinrich; Bunnenberg, Edward; Shu, Arthur Y.L.; Tolf, Bo-Ragnar; Djerassi, Carl [Journal of the American Chemical Society, 1993, vol. 115, # 11, p. 4554 - 4565]

14
[ 2386-25-6 ]
[ 4659-45-4 ]
[ 95883-30-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In N,N-dimethyl-formamide for 16h; Ambient temperature;

Reference： [1]Itahara, Toshio; Kawasaki, Kazukuni; Ouseto, Fumio [Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 11, p. 3488 - 3493]

15
[ 2386-25-6 ]
[ 625-82-1 ]
[ 628-35-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With ethylene glycol In benzene for 0.25h; Heating;

Reference： [1]Moon, M. W.; Wade, R. A. [Journal of Organic Chemistry, 1984, vol. 49, # 15, p. 2663 - 2669]

16
[ 2386-25-6 ]
[ 5866-63-7 ]
[ 172614-52-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With acetic acid for 1h; Heating;

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

18
[ 2386-25-6 ]
[ 932-87-6 ]
1-(2,4-dimethyl-1-phenylethynyl-1H-pyrrol-3-yl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium phosphate; 1,10-Phenanthroline; copper (II) sulfite In toluene at 70 - 80℃;
50%	With potassium phosphate; 1,10-Phenanthroline; copper(II) sulfate In toluene at 70 - 80℃;

Reference： [1]Zhang, Yanshi; Hsung, Richard P.; Tracey, Michael R.; Kurtz, Kimberly C. M.; Vera, Eymi L. [Organic Letters, 2004, vol. 6, # 7, p. 1151 - 1154]
[2]Trofimov, Boris A.; Stepanova, Zinaida V.; Sobenina, Lyubov' N.; Mikhaleva, Al'bina I.; Ushakov, Igor A. [Tetrahedron Letters, 2004, vol. 45, # 34, p. 6513 - 6516]

19
[ 2386-25-6 ]
[ 591-50-4 ]
1-(2,4-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 24h;

Reference： [1]Antilla, Jon C.; Baskin, Jeremy M.; Barder, Timothy E.; Buchwald, Stephen L. [Journal of Organic Chemistry, 2004, vol. 69, # 17, p. 5578 - 5587]

20
1-{5-[(benzyl-hydroxy-amino)-phenyl-methyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone [ No CAS ]
[ 2386-25-6 ]
1-(5-((4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)methyl)-2,4-dimethyl-1H-pyrrol-3-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol at 0℃; for 1h;

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]

21
[ 2386-25-6 ]
[ 3376-26-9 ]
1-{5-[(benzyl-hydroxy-amino)-phenyl-methyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride In methanol at -40℃; for 24h;

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]

22
[ 2386-25-6 ]
[ 3376-26-9 ]
1-{5-[(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)methyl]-2,4-dimethyl-1H-pyrrol-3-yl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogenchloride In methanol at 20℃; for 3.5h;
90%	With methanol; acetyl chloride at 20℃; for 3.5h;	2 1-{5-[4-Acetyl-3,5-dimethyl-1H-pyrrol-2-yl)(phenyl)methyl]-2,4-dimethyl-1H-pyrrol-3-yl}ethan-1-one General procedure: [0200] Freshly distilled acetyl chloride (2 equiv.) was added dropwise at 0°C to anhydrous methanol and the mixturewas stirred for 15 min to form in situ hydrogen chloride (2 equiv.). The appropriate nitrone 2 (1 equiv.) was added followedby pyrrole 1 (2 equiv.). The reaction mixture was then warmed to the appropriate temperature and stirred until completedisappearance of the starting material (followed by TLC). The mixture was then treated with saturated aqueous NaHCO3solution up to pH 8-9. The aqueous layer was extracted three times with CH2Cl2. The combined organic layers werewashed with brine, dried over anhydrous MgSO4 and concentrated. The obtained 2,2’-bis(pyrrolyl)alkane (3) was purifiedby flash chromatography on silica gel (pre-treated with 3% of triethylamine, v/v). [0204] Prepared according to the above general procedure starting from 78 mg of nitrone 2b (0.37 mmol) in 5.0 mL of MeOH, 101 mg of pyrrole 1a (0.73 mmol) and 57 mg of acetyl chloride (0.73 mmol). The mixture was stirred at room temperature for 3.5 hours. Purification (eluent: pentane/EtOAc, 6/4 to 2/8) afforded 2,2'-bis(pyrrolyl)alkane 3b (121 mg, 0.33 mmol, 90%) as an orange foam. IR (KBr disc): 3290, 3090, 3060, 3020, 2960, 2920 2240, 1730, 1630, 1470, 1440, 1420, 1380, 1240, 1110, 1070, 1050, 950, 910, 730 cm-1. 1H NMR (300 MHz, CDCl3) δ 2.13 (s, 6H, 2CH3), 2.33 (s, 6H, 2CH3), 2.36 (s, 6H, 2CH3), 5.56 (s, 1H, H-1), 7.04-7.05 (m, 2H, Harom), 7.20-7.30 (m, 3H, Harom), 8.56 (s, 2H, NH). 13C NMR (75 MHz, CDCl3) δ 11.8 (CH3), 15.1 (CH3), 30.8 (CH3), 38.3 (C-1), 116.6 (Cpyrr), 121.6 (Cpyrr), 126.2 (Cpyrr), 126.9 (CHarom), 128.0 (CHarom), 128.8 (CHarom), 134.4 (Cpyrr), 140.7 (Carom), 196.0 (C=O). LRMS (ESI+): m/z 385 [(M+Na)+], 363 [(M+H)+].

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]
[2]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; CENTRE HOSPITALIER UNIVERSITAIRE DE GRENOBLE; COMMUNITY GRENOBLE ALPES UNIVERSITY - EP2626357, 2013, A1 Location in patent: Paragraph 0200; 0203; 0204

23
[ 2386-25-6 ]
[ 105623-16-3 ]
1-{5-[1-(benzyl-hydroxy-amino)-propyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride In methanol at -20℃; for 4h;

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]

24
[ 2386-25-6 ]
[ 105623-16-3 ]
1-{5-[1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)propyl]-2,4-dimethyl-1H-pyrrol-3-yl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogenchloride In methanol at 20℃; for 3h;

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]

25
[ 2386-25-6 ]
[ 105623-16-3 ]
1-{5-[1-(benzyl-hydroxy-amino)-propyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone [ No CAS ]
1-{5-[1-(4-acetyl-3,5-dimethyl-1H-pyrrol-2-yl)propyl]-2,4-dimethyl-1H-pyrrol-3-yl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride In methanol at 0℃; for 2h; Title compound not separated from byproducts;

Reference： [1]Berini, Christophe; Minassian, Frédéric; Pelloux-Léon, Nadia; Vallée, Yannick [Tetrahedron Letters, 2005, vol. 46, # 50, p. 8653 - 8656]

26
[ 2386-25-6 ]
[ 25016-02-8 ]
1-{5-[(4-acetyl-3,5-dimethyl-pyrrol-2-ylidene)-(2-methoxy-5-nitro-phenyl)-methyl]-2,4-dimethyl-1H-pyrrol-3-yl}-ethanone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10640 - 10641

27
[ 2386-25-6 ]
[ 98-59-9 ]
1-{2,4-dimethyl-1-[(4-methylphenyl)sulfonyl]-1H-pyrrol-3-yl}ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 2,4-dimethyl-3-acetylpyrrole With sodium hydride In tetrahydrofuran at 0 - 20℃; for 0.416667h; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 20℃; for 12h;
26%	Stage #1: 2,4-dimethyl-3-acetylpyrrole With potassium In tetrahydrofuran Heating; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran at 20℃; for 12h;

Reference： [1]Horsten, Tomas; De Jong, Flip; Theunissen, Dries; Van Der Auweraer, Mark; Dehaen, Wim [Journal of Organic Chemistry, 2021, vol. 86, # 19, p. 13774 - 13782]
[2]Loughlin, Wendy A.; Henderson, Luke C.; Elson, Kathryn E.; Murphy, Michelle E. [Synthesis, 2006, # 12, p. 1975 - 1980]

28
[ 2386-25-6 ]
[ 98-80-6 ]
1-(2,4-dimethyl-1-phenyl-1H-pyrrol-3-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
7%	With copper diacetate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 240h;

Reference： [1]Bekolo, Henri [Canadian Journal of Chemistry, 2007, vol. 85, # 1, p. 42 - 46]

29
[ 2386-25-6 ]
[ 25016-02-8 ]
4,4-difluoro-2,6-diacetyl-8-(2-methoxy-5-nitrophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5597 - 5604

30
[ 2386-25-6 ]
4,4-difluoro-2,6-diacetyl-8-(5-amino-2-methoxyphenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / CH₂Cl₂ / 20 °C 1.2: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ 1.3: 9.3 percent / BF₃*OEt₂; N,N-diisopropylethylamine / CH₂Cl₂ / 3 h / 20 °C 2.1: 42 percent / H₂ / Pd/C / methanol; CH₂Cl₂

Reference： [1]Sunahara, Hisato; Urano, Yasuteru; Kojima, Hirotatsu; Nagano, Tetsuo [Journal of the American Chemical Society, 2007, vol. 129, # 17, p. 5597 - 5604]

31
[ 2386-25-6 ]
4,4-difluoro-2,6-diacetyl-8-(2-methoxy-5-nitrophenyl)-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / CH₂Cl₂ / 20 °C 1.2: 2,3-dichloro-5,6-dicyano-p-benzoquinone / CH₂Cl₂ 2.1: diisopropylethylamine; BF₃*OEt₂ / toluene / 20 °C

Reference： [1]Ueno, Tasuku; Urano, Yasuteru; Kojima, Hirotatsu; Nagano, Tetsuo [Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10640 - 10641]

32
[ 2386-25-6 ]
[ 172614-53-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

33
[ 2386-25-6 ]
[ 172614-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

34
[ 2386-25-6 ]
2,7,12,13,17,18-Hexamethyl-3-propyl-8-vinylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

35
[ 2386-25-6 ]
2,7,12,13,17,18-Hexamethyl-3-propylporphyrin-8-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

36
[ 2386-25-6 ]
8-Ethyl-2,7,12,13,17,18-hexamethyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

37
[ 2386-25-6 ]
8-Acetyl-2,7,12,13,17,18-hexamethyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

38
[ 2386-25-6 ]
2,7,12,13,17,18-Hexamethyl-8-neopentyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

39
[ 2386-25-6 ]
2,7,12,13,17,18-Hexamethyl-3,8-dipropylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

40
[ 2386-25-6 ]
1-((4Z,10Z,15Z,19Z)-3,8,12,13,17,18-Hexamethyl-7-propyl-22,24-dihydro-porphin-2-yl)-ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

41
[ 2386-25-6 ]
8-Isobutyl-2,7,12,13,17,18-hexamethyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

42
[ 2386-25-6 ]
8-Butyl-2,7,12,13,17,18-hexamethyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

43
[ 2386-25-6 ]
2,7,12,13,17,18-Hexamethyl-8-pentyl-3-propylporphyrin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine 9: 10percent aq. NaIO₄ / pyridine / 60 °C

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

44
[ 2386-25-6 ]
1-((4Z,10Z,15Z,19Z)-3,8,12,13,17,18-Hexamethyl-7-propyl-22,24-dihydro-porphin-2-yl)-ethane-1,2-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature 5: 1.) (AcO)2Cu, AcONa, AcOH 2.) CF₃COOH, 18 M H₂SO₄ / 1.) MeOH, heating, overnight, 2.) r.t., 1 h 6: NaBH₄ / ethanol; CHCl₃ / 1 h / Ambient temperature 7: PhCOCl / dimethylformamide / 1.5 h / Heating 8: OsO₄ / pyridine

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

45
[ 2386-25-6 ]
(5-{5-[1-[5-(4-Acetyl-3,5-dimethyl-1H-pyrrol-2-ylmethyl)-3-methyl-4-propyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-3,4-dimethyl-5H-pyrrol-2-ylmethyl}-3,4-dimethyl-1H-pyrrol-2-ylmethylene)-dimethyl-ammonium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 81 percent / AcOH / 1 h / Heating 2: 90 percent / H₂, Et₃N / 10percent Pd/C / ethanol / 2 h 3: 58 percent / aq. CF₃COOH, CH(OEt)3 4: CF₃COOH / methanol / 0.33 h / Ambient temperature

Reference： [1]Atkinson, Errol J.; Clezy, Peter S.; Leung, Christopher W. F.; Ramadan, Saadallah; Salek, Abdoreza; Zhuo, Minxing [Australian Journal of Chemistry, 1995, vol. 48, # 11, p. 1873 - 1886]

46
[ 2386-25-6 ]
3-(1-hydroxy-ethyl)-2,4-dimethyl-pyrrolidine-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium; toluene / und Behandeln der Reaktionsloesung mit Chlorokohlensaeure-aethylester 2: Raney nickel; dioxane / 180 °C / Hydrogenation

Reference： [1]Rainey; Adkins [Journal of the American Chemical Society, 1939, vol. 61, p. 1104,1105]

47
[ 2386-25-6 ]
3-acetyl-2,4-dimethyl-pyrrolidine-1-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium; toluene / und Behandeln der Reaktionsloesung mit Chlorokohlensaeure-aethylester 2: Raney nickel; dioxane / 100 °C / Hydrogenation_.unter Druck

Reference： [1]Rainey; Adkins [Journal of the American Chemical Society, 1939, vol. 61, p. 1104,1105]

48
[ 123-54-6 ]
[ 2386-25-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid; aqueous NaNO₂; zinc-powder / Reaktion ueber zwei Stufen 2: Raney nickel; methanol / 110 - 120 °C / 73550.8 Torr / Hydrogenation
	Multi-step reaction with 2 steps 1.1: sodium nitrite; acetic acid / water / 4 h / 20 °C / Cooling with ice 1.2: 1 h / 60 °C / Cooling with ice 2.1: potassium hydroxide / ethylene glycol / 4 h / 160 °C
	Multi-step reaction with 3 steps 1: neat (no solvent) / 2 h / 20 °C 2: dmap / acetonitrile / 2 h / 50 °C / Inert atmosphere 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.08 h / 70 °C / Inert atmosphere

	Multi-step reaction with 2 steps 1.1: acetic acid; sodium nitrite / water / 12 h / 0 - 25 °C 1.2: 1 h / 60 °C / Cooling with ice 2.1: potassium hydroxide / 1,2-dimethoxyethane / 4 h / 160 °C
	Multi-step reaction with 2 steps 1.1: sodium nitrite; acetic acid / water / 3 h / 0 - 20 °C 1.2: 4 h / 0 - 85 °C 2.1: potassium hydroxide / ethylene glycol / 3 h / 140 °C

Reference： [1]Johnson et al. [Journal of the Chemical Society, 1958, p. 4254][Org. Synth. Coll. Vol. V. <1973> 1022]
[2]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN103626793, 2016, B
[3]Chikayuki, Yuya; Higashiyama, Kimio; Ishikawa, Haruka; Kouno, Yasuaki; Sasaki, Shigeru; Teramoto, Hiroyoshi; Waki, Yoko; Yamauchi, Takayasu; Yonekawa, Shiori [Heterocycles, 2020, vol. 100, # 5, p. 719 - 746]
[4]Chen, Ji-An; Gao, Jie; Gu, Xianfeng; Li, Mimi; Tan, Jiahui; Yin, Xiaofan; Zhao, Zhen [Organic and biomolecular chemistry, 2020, vol. 18, # 25, p. 4744 - 4747]
[5]Bian, Yuanyuan; Chen, Yadong; Hong, Qianqian; Jiang, Fei; Kong, Bo; Li, Hongmei; Lu, Tao; Ma, Yu; Ran, Ting; Tang, Weifang; Wang, Cong; Yang, Na; Zhang, Zhimin; Zheng, Wan; Zhu, Jiapeng; Zhu, Zhaohong [European Journal of Medicinal Chemistry, 2022, vol. 227]

49
[ 2386-25-6 ]
[ 76513-69-4 ]
3-acetyl-2,4-dimethyl-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With NaH; sodium hydrogencarbonate In N,N-dimethyl-formamide	45.A 3-Acetyl-2,4-dimethyl-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole (Step 1) Method A 3-Acetyl-2,4-dimethyl-1-{2-(trimethylsilyl)ethoxymethyl}-1H-pyrrole (Step 1) To a stirred solution of 3-acetyl-2,4-dimethyl-1H-pyrrole (commercially available from Aldrich Chem. Co. Inc., 1.50 g, 10.6 mmol) in DMF (40 mL) was added NaH (60% oil dispersion, 0.85 g, 21.2 mmol) at room temperature under nitrogen. After stirring for 30 minutes at room temprature the resulting suspension was cooled to 0° C. and added 2-(trimethylsilyl)ethoxymethyl chloride (3 mL, 15.9 mmol). The reaction mixture was warm to room temperature and stirred for 3 hours. The mixture was quenched with aqueous saturated NaHCO3 solution, and the whole extracted with diethyl ether (100 mL*2). The combined organic layers were washed with brine (50 mL), dried over MgSO4, concentrated in vacuo. Chromatographic purification of the crude product eluding ethyl acetate-hexane (1:10) gave the subtitle product (2.32 g, 82% yield). 1H-NMR (CDCl3) δ 6.37 (s, 1H), 5.09 (s, 2H), 3.44 (t, J=8.1 Hz, 2H), 2.50 (s, 3H), 2.40 (s, 3H), 2.22 (s, 3H), 0.87 (t, J=8.1 Hz, 2H), -0.04 (s, 9H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2002/49235, 2002, A1

50
[ 2386-25-6 ]
[ 6303-21-5 ]
[ 110-13-4 ]
[ 20884-56-4 ]