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CAS No. : | 4600-86-6 | MDL No. : | MFCD09033195 |
Formula : | C13H16O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IIJPVOVAVTZFRH-UHFFFAOYSA-N |
M.W : | 188.27 | Pubchem ID : | 11030576 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With sulfuric acid at 95℃; for 3h; | 162.B Step B.: Preparation of 5-fe/f-butyl-indan-1-one.; The title compound of Step A (1.3 g, 5.8 mmol) was dissolved in cone. H2SO4 (10 ml_) and heated at 95 0C for 3 h. The reaction mixture was cooled to rt, poured onto ice, and extracted with Et2O (3 x 25 ml_). The combined organic extracts were washed with sat'd NaHCO3 (aq.) and dried to provide the title compound (0.74 g, 68%). MS (ESI): mass calcd. for Ci3Hi6O, 188.1 ; m/z found, 189.2 [M+H]+. 1H NMR (CDCI3): 7.67 - 7.58 (m, 1 H), 7.44 - 7.32 (m, 2H), 3.09 - 3.02 (m, 2H), 2.65 - 2.68 (m, 2H), 1.27 (d, J = 8.5 Hz, 9H). |
64% | With sulfuric acid at 95℃; for 2h; | |
60% | With sulfuric acid at 20℃; for 3h; | 26.315.2 3.15.2 3.15.2 Preparation of 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one (940-3) A mixture of 1-(4-(tert-butyl)phenyl)-3-chloropropan-1-one (6.0 g, 26.7 mmol) in conc. H2SO4(37 mL) was stirred at room temperature for 3 hrs before poured into ice water (20 mL), extracted with DCM (50 mL*2). The combined organic layers were washed with water (20 mL*2), dried, filtered and concentrated to give the residue which was purified by flash chromatography (silica gel, 0˜10% ethyl acetate in petroleum ether) to afford the product 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one (940-3) (3 g, 60%). LC-MS (ESI): m/z (M+1) 189.36. |
With sulfuric acid | ||
With sulfuric acid for 2.5h; Heating; | ||
With sulfuric acid at 100℃; for 2.5h; | 81 l-(4-tert-Butyl-phenyl)-3-chloro-propan-l-one (45.6g, 447 mmol) was taken up in concentrated sulfuric acid (20OmL) and the resulting mixture was heated to 100 0C with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to RT, the reaction mixture was very carefully poured onto about IKg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about RT. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2X200mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5X300mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764g). | |
With sulfuric acid at 100℃; for 2.5h; | 23 5-tert-Butyl-indan-1-one Example 23 5-tert-Butyl-indan-1-one 1-(4-tert-Butyl-phenyl)-3-chloro-propan-1-one (45.6 g, 447 mmol) was taken up in concentrated sulfuric acid (200 mL) and the resulting mixture was heated to 100° C. with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to room temperature, the reaction mixture was very carefully poured onto about 1 Kg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about room temperature. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2*200 mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5*300 mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764 g). | |
With sulfuric acid at 100℃; for 2.5h; | 116; 118 5-tert-Butyl-indan-1-one 1-(4-tert-Butyl-phenyl)-3-chloro-propan-1-one (45.6 g, 447 mmol) was taken up in concentrated sulfuric acid (200 mL) and the resulting mixture was heated to 100° C. with stirring for 2.5 hours. TLC indicated that all of the starting material had been consumed. After cooling to room temperature, the reaction mixture was very carefully poured onto about 1 Kg of crushed ice. Then some diethyl ether was added and the mixture was stirred carefully until it had cooled to about room temperature. Ethyl acetate (1200 mL) was added and after partitioning, the layers were separated. The acidic layer was then further extracted with ethyl acetate (2*200 mL). The combined ethyl acetate layers were washed with saturated sodium bicarbonate (5*300 mL). Finally the ethyl acetate layer was dried over magnesium sulfate, filtered, concentrated and pumped to dryness to afford the title compound as a colorless oil (15.764 g). | |
With sulfuric acid at 95℃; for 2.5h; | 56.E EXAMPLE 56E 5-tert-butyl-1-indanone; Example 56D (22.25 g, 99 mmol) was dissolved in concentrated sulfuric acid (100 ml) and heated on a water bath at 95° C. for 2.5 hours. The reaction mixture was cooled, poured onto ice, and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. | |
With sulfuric acid In dichloromethane at 90℃; for 2h; | 6.2 Step 2: Sulfuric acid (448 ml, 5 times) was slowly heated to 90°C, a solution of 1 -(4-tert- butylphenyl)-3-chloropropan-1-one (88 g, 390 mmol) in dichloromethane (176 ml, 2 times) was added drop wise for 1 h and stirred the reaction contents for 1 h at the sametemperature. On completion of the reaction, poured the reaction contents into crushed ice (500 g) and the product extracted with ethyl acetate (3 * 300 ml). Combined extract was washed with 5% sodium carbonate (2 * 100 ml) and washed with water (200 ml). Dried the contents over sodium sulfate and concentrated under reduced pressure to obtain the crude product as a pale yellow colored liquid (72 g, crude). | |
With sulfuric acid | ||
3.7 kg | With sulfuric acid In dichloromethane at 90℃; for 2h; Large scale; | |
With sulfuric acid at 95℃; for 2.5h; | 1B EXAMPLE 1B 5-tert-butyl-1-indanone [0192] 1-(4-tert-Butylphenyl)-3-chloro-1-propanone (22.25 g, 99 mmol) was dissolved in concentrated sulfuric acid (100 ml) and heated on a water bath at 95° C. for 2.5 hours. The reaction mixture was cooled, poured onto ice, and extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen fluoride | ||
With hydrogen fluoride at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium hydroxide In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine In diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: trimethyl phosphonoacetate; 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one With sodium methylate In methanol; Petroleum ether at 20℃; for 24h; and reflux, 17 h; Stage #2: With hydrogen In ethyl acetate at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium methylate In methanol; Petroleum ether at 20℃; for 24h; and reflux, 17 h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydride In toluene at 60℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 72 percent / LiAlH4 / diethyl ether / 1.5 h / 20 °C 2: 96 percent / KHSO4 / 0.5 h / 160 °C / 75.01 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: NaH / toluene / 8 h / 60 °C 2: 86 percent / H2 / 5 percent Pd/C / ethyl acetate / 12 h / 20 °C / 760 Torr 3: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating 4: 72 percent / PCC / CH2Cl2 / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: NaOMe / petroleum ether; methanol / 24 h / 20 °C / and reflux, 17 h 1.2: H2 / 5 percent Pd/C / ethyl acetate / 1 h / 20 °C / 760 Torr 2.1: 99 percent / LiAlH4 / diethyl ether / 2 h / Heating 3.1: 62 percent / PCC / CH2Cl2 / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: NaH / toluene / 8 h / 60 °C 2: K2CO3 / tetrahydrofuran / 3 h / Heating 3: H2 / 10 percent Pd/C / acetic acid / 408 h / 20 °C / 760 Torr 4: LiAlH4 / diethyl ether / 48 h / Heating 5: PCC / CH2Cl2 / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaH / toluene / 8 h / 60 °C 2: 86 percent / H2 / 5 percent Pd/C / ethyl acetate / 12 h / 20 °C / 760 Torr 3: 100 percent / LiAlH4 / diethyl ether / 2 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaOMe / petroleum ether; methanol / 24 h / 20 °C / and reflux, 17 h 1.2: H2 / 5 percent Pd/C / ethyl acetate / 1 h / 20 °C / 760 Torr 2.1: 99 percent / LiAlH4 / diethyl ether / 2 h / Heating | ||
7 Preparation of 5-tert-butyl-1-indanacetaldehyde Odor: metallic, floral. The starting 2-(5-tert-butyl-1-indanyl)-1-ethanol was prepared from 5-tert-butyl-1-indanone [ex. 4 a)], as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: NaH / toluene / 8 h / 60 °C 2: K2CO3 / tetrahydrofuran / 3 h / Heating 3: H2 / 10 percent Pd/C / acetic acid / 408 h / 20 °C / 760 Torr 4: LiAlH4 / diethyl ether / 48 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaH / toluene / 8 h / 60 °C 2: 86 percent / H2 / 5 percent Pd/C / ethyl acetate / 12 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaH / toluene / 8 h / 60 °C 2: K2CO3 / tetrahydrofuran / 3 h / Heating 3: H2 / 10 percent Pd/C / acetic acid / 408 h / 20 °C / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: NaH / toluene / 8 h / 60 °C 2: K2CO3 / tetrahydrofuran / 3 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 73 percent / AlCl3 / CH2Cl2 / 4 h / Ambient temperature 2: 64 percent / concd H2SO4 / 2 h / 95 °C | ||
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 0.25 h / 0 °C 1.2: 1.25 h / 0 °C 1.3: Cooling with ice 2.1: sulfuric acid / dichloromethane / 2 h / 90 °C | ||
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane 2: sulfuric acid |
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 2: sulfuric acid / 3 h / 20 °C | ||
Multi-step reaction with 2 steps 1: aluminum (III) chloride / dichloromethane / 16 h / 0 - 20 °C 2: sulfuric acid / 2.5 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Br2 / diethyl ether 2: P4S10 / toluene / 1.5 h / 90 - 100 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine at 20℃; for 16h; | ||
With pyridine at 20℃; for 16h; | 56.F EXAMPLE 56F 5-tert-butyl-1-indanone O-methyloxime; Example 56E (13.41 g, 71.23 mmol) and methoxyamine hydrochloride (6.68 g, 80 mmol) were dissolved in pyridine (75 ml) and stirred at ambient temperature for 16 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between water and diethyl ether. The combined organic layers were washed with 1N aqueous hydrochloric acid, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. | |
With pyridine at 20℃; for 16h; | 1C EXAMPLE 1C 5-tert-butyl-1-indanone O-methyloxime [0193] 5-tert-Butyl-1-indanone (13.41 g, 71.23 mmol) and methoxyamine hydrochloride (6.68 g, 80 mmol) were disolved in pyridine (75 ml) and stirred at ambient temperature for 16 hours. The mixture was evaporated under reduced pressure and the residue was partitioned between water and diethyl ether (×2). The combined organic layers were washed with 1N aqueous hydrochloric acid, dried with magnesium sulfate, and the filtrate was evaporated under reduced pressure to provide the title compound which was used without further purification in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In dichloromethane; Petroleum ether | 4.a a a 5-tert-butyl-1-indanone To a solution of tert-butylbenzene (88.9 g, 0.7mole) and of 3-chloropropionyl chloride (Fluka, 93.8 g, 0.7 mole) in CH2 Cl2 (105 ml), at 0°, there was added portionwise AlCl3 (95.7 g, 0.7 mole) over 2 h. After 3 h at 0°, the mixture was poured on ice and diluted with CH2 Cl2 (200 ml). The organic phase was washed with water (2 times) and concentrated. The residue was dissolved in ether, washed with aq. sat. NaHCO3 and brine, dried over Na2 SO4 and concentrated (152 g). Crystallizing in petroleum ether 30°-50°, at -30°, provided colorless crystals (117 g, purity>99%, yield 52%) of 1-(4-tert-butyl-1-phenyl)-3-chloro-1-propanone. M.p. 35-37° NMR(1 H, 360 MHz, CDCl3): 7.90(d, J=8, 2H); 7.49(d, J=8, 2H); 3.92(t, J=7, 2H; 3.43(t, J=7, 2H); 1.34(s, 9H)δ ppm NMR(13 C, 90.5 MHz, CDCl3): 196.2(s); 157.3(s); 133.7(s); 128.0(2d); 125.7(2d); 41.1(t); 38.8(t); 35.1(s); 31.0(3q)δ ppm MS: 224(M+, 4), 209(13), 173(9), 161(100), 146(7), 118(9), 91(11), 77(4), 63(5), 41(2) |
Stage #1: 2-chloropropionyl chloride With aluminum (III) chloride In dichloromethane at 0 - 5℃; Inert atmosphere; Stage #2: tert-butylbenzene In dichloromethane at 0 - 5℃; for 1.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-fluoro-4-hydroxy-1,4-diazoniabicyclo[2,2,2]octane-1,4-bis(tetrafluoroborate) In methanol for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; isopentyl nitrite In methanol at 20℃; for 44h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.1% | With sodium azide In methanesulfonic acid; dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; | 26.15.3 3.15.3 3.15.3 Preparation of 6-(tert-butyl)-3,4-dihydroisoquinolin-1(2H)-one (940-4) To a solution of 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one (1.0 g, 5.3 mmol) in dry DCM (10 mL) and methanesulfonicacid (6 mL) was added sodium azide (690 mg, 10.6 mmol) at 0° C. under N2. After being stirred at room temperature for 2 hrs, the reaction mixture was quenched with sat.NaHCO3 (20 mL) at 0° C., extracted with DCM (20 mL*2). The combined organic layers were washed with water (10 mL*2), dried, filtered and concentrated to give the residue which was purified by flash chromatography (silica gel, 0˜10% ethyl acetate in petroleum ether) to afford the product 6-(tert-butyl)-3,4-dihydroisoquinolin-1 (2H)-one (940-4) (600 mg, 56.1%). LC-MS (ESI): m/z (M+1) 204.36. |
Stage #1: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one With sodium azide; methanesulfonic acid In dichloromethane at 0℃; for 2.75h; Stage #2: With water; sodium hydroxide In dichloromethane at 0℃; | 82 To 5-tert-Butyl-indan-l-one (15.7g, 83.4mmol) in DCM (150 mL) was added methanesulfonic acid (10OmL) and the resulting mixture was cooled to 0 0C. Then sodium azide (10.83g, 2 eq) was added carefully portion- wise over 15 minutes. The resulting mixture was stirred at 00C for about 2.5 hours. TLC analysis confirmed that all of the 5-tert-Butyl-indan-l-one had been consumed. With stirring at 00C was added very carefully a solution of aqueous sodium hydroxide (20%) until pH = 14. Then added DCM (1000 mL) and water (500 mL) which results in a large emulsion. The layers were separated and the aqueous layer was further extracted with dichloro- methane (2X200mL). Finally the combined DCM layers were washed with brine (9X200mL), dried over magnesium sulfate and filtered through a bed of celite. After concentrating and pumping to dryness there was 13.5g of crude product as a tan solid. Purification on a 400 g Analogix Column eluting with a gradient of 10% to 60% ethyl acetate in hexane provided the correct isomer as a white powder (7.22g) ((M+H)+ =204) and the undesired isomer (1.555g) as a white powder. | |
Stage #1: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one With sodium azide; methanesulfonic acid In dichloromethane at 0℃; for 2.75h; Stage #2: With sodium hydroxide In dichloromethane; water at 0℃; | 24 6-tert-Butyl-3,4-dihydro-2H-isoquinolin-1-one Example 24 6-tert-Butyl-3,4-dihydro-2H-isoquinolin-1-one To 5-tert-Butyl-indan-1-one (15.7 g, 83.4 mmol) in dichloromethane (150 mL) was added methanesulfonic acid (100 mL) and the resulting mixture was cooled to 0° C. Then sodium azide (10.83 g, 2 eq) was added carefully portion-wise over 15 minutes. The resulting mixture was stirred at 0° C. for about 2.5 hours. TLC analysis confirmed that all of the 5-tert-Butyl-indan-1-one had been consumed. With stirring at 0° C. was added very carefully a solution of aqueous sodium hydroxide (20%) until pH=14. Then added dichloromethane (1000 mL) and water (500 mL) which results in a large emulsion. The layers were separated and the aqueous layer was further extracted with dicholormethane (2*200 mL). Finally the combined dichloromethane layers were washed with brine (9*200 mL), dried over magnesium sulfate and filtered through a bed of celite. After concentrating and pumping to dryness there was 13.5 g of crude product as a tan solid. Purification on a 400 g Analogix Column eluding with a gradient of 10% to 60% ethyl acetate in hexane provided the correct isomer as a white powder (7.22 g) ((M+H)+=204) and the undesired isomer (1.555 g) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one With sodium azide; methanesulfonic acid In dichloromethane at 0℃; for 2.75h; Stage #2: With sodium hydroxide In dichloromethane; water | 119 6-tert-Butyl-3,4-dihydro-2H-isoquinolin-1-one To 5-tert-Butyl-indan-1-one (15.7 g, 83.4 mmol) in dichloromethane (150 mL) was added methanesulfonic acid (100 mL) and the resulting mixture was cooled to 0° C. Then sodium azide (10.83 g, 2 eq) was added carefully portion-wise over 15 minutes. The resulting mixture was stirred at 0° C. for about 2.5 hours. TLC analysis confirmed that all of the 5-tert-Butyl-indan-1-one had been consumed. With stirring at 0° C. was added very carefully a solution of aqueous sodium hydroxide (20%) until pH=14. Then added dichloromethane (1000 mL) and water (500 mL) which results in a large emulsion. The layers were separated and the aqueous layer was further extracted with dicholormethane (2*200 mL). Finally the combined dichloromethane layers were washed with brine (9*200 mL), dried over magnesium sulfate and filtered through a bed of celite. After concentrating and pumping to dryness there was 13.5 g of crude product as a tan solid. Purification on a 400 g Analogix Column eluding with a gradient of 10% to 60% ethyl acetate in hexane provided the correct isomer as a white powder (7.22 g) ((M+H)|=204) and the undesired isomer (1.555 g) as a white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: hydroxylamine hydrochloride; sodium acetate / methanol / 2 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C 2.2: 0 - 20 °C 3.1: hydrogen; ammonia / palladium 10% on activated carbon / methanol / 6 h / 3102.97 Torr | ||
With ammonia | ||
Multi-step reaction with 2 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride; sodium acetate / methanol / 2 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C 2.2: 0 - 20 °C 3.1: hydrogen; ammonia / palladium 10% on activated carbon / methanol / 6 h / 3102.97 Torr 4.1: N-Ac-Leu / methanol / 1 h / 65 °C | ||
Multi-step reaction with 3 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3: N-Ac-Leu / methanol / 1 h / 65 °C / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydroxylamine hydrochloride; sodium acetate / methanol / 2 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C 2.2: 0 - 20 °C 3.1: hydrogen; ammonia / palladium 10% on activated carbon / methanol / 6 h / 3102.97 Torr 4.1: N-acetyl-D-leucine / methanol / 1 h / 65 °C | ||
Multi-step reaction with 3 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3: N-acetyl-D-leucine / methanol / Heating / reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydroxylamine hydrochloride; sodium acetate / methanol / 2 h / Reflux 2.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 20 °C 2.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol for 2h; Reflux; | 6.3 Step 3: To a stirred solution of 5-tert-butyl-2,3-dihydro-1 H-inden-1-one (75 g, 390 mmol) in methanol (375 ml, 5 times), hydroxylamine hydrochloride (33.2 g, 470 mmoles, 1.2 eq), sodium acetate (39.2 g, 470 mmol, 1.2 eq) were added. The reaction mixture was heated to reflux for 2 h. On completion of the reaction, methanol was distilled off completely, residue was taken in ice water (300 ml) and stirred for 1 h. Filtered the contents and the solid obtained was washed with water (2 χ 200 ml). Filtered solid was taken in hexane (300 ml), stirred for 30 min and filtered again. The solid was washed with hexane (2 χ 100 ml) and dried to obtain the product as a pale yellow colored liquid (65 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; isopentyl nitrite In water; benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride; isopentyl nitrite / water; benzene 2: ammonium hydroxide; sodium dithionite / ethanol / 24 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; isopentyl nitrite / water; benzene 2: ammonium hydroxide; sodium dithionite / ethanol / 24 h / Reflux; Inert atmosphere 3: sodium dichromate dihydrate; acetic anhydride; acetic acid / 24 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride; isopentyl nitrite / water; benzene 2: ammonium hydroxide; sodium dithionite / ethanol / 24 h / Reflux; Inert atmosphere 3: sodium dichromate dihydrate; acetic anhydride; acetic acid / 24 h / Inert atmosphere; Reflux 4: dimethyl sulfoxide / 20 °C / Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene / 760.05 Torr / Reflux 2: sodium tris(acetoxy)borohydride / methanol / 93 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia 2: water; methanol / 1 h / 65 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ammonia 2: water; methanol / 1 h / 65 °C / Large scale 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia 2: methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ammonia 2: methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: toluene / 760.05 Torr / Reflux 2.1: sodium tetrahydroborate / ethanol / 10 °C / Large scale 2.2: 65 °C / Large scale |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: ammonia 2: water; methanol / 1 h / 65 °C / Large scale 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 1 h / 20 °C 4: sodium hydroxide / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With toluene-4-sulfonic acid; propionic acid In toluene at 135℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium azide / dichloromethane; methanesulfonic acid / 2 h / 0 - 20 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridine / 16 h / 20 °C 2.1: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3.1: toluene / 3 h / Heating / reflux 3.2: 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3: diethyl ether / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3: diethyl ether / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / 16 h / 20 °C 2: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3: diethyl ether / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pyridine / 16 h / 20 °C 2.1: ammonia; hydrogen / palladium 10% on activated carbon / methanol; water / 16 h / 50 °C / 3102.97 Torr 3.1: toluene / 3 h / Heating / reflux 3.2: 16 h / 20 °C 4.1: sodium hydroxide / tetrahydrofuran; methanol / 0.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one; phenylhydrazine With toluene-4-sulfonic acid In ethanol for 0.666667h; Reflux; Stage #2: With sulfuric acid In ethanol for 12h; Reflux; | 2.3.1.1. 2-isopropyl-5,10-dihydroindeno[1,2-b]indole General procedure: The solution of PhNHNH2 (30.2 mL, 0.28 mol), 5-isopropyl-1-indanone (48.8 g,0.28 mmol) and p-TsOH (0.5 g) in EtOH (250 mL) was refluxed for40 min and cooled in an ice/water external bath. A solution of H2SO4(100 mL) in EtOH (500 mL) was added. The mixture was refluxed for12 h, cooled and poured into the solution of NaOH (40 g, 1 mol) in 2 Lof ice water. The precipitate was filtered off, washed with water anddried. The yield was 60.1 g (87%), and the product was a beige powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: toluene-4-sulfonic acid / ethanol / 0.67 h / Reflux 1.2: 12 h / Reflux 2.1: sodium hydroxide; cetyltrimethylammonim bromide / benzene; water / 5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / ethanol / 0.67 h / Reflux 1.2: 12 h / Reflux 2.1: sodium hydroxide; cetyltrimethylammonim bromide / benzene; water / 5 h 3.1: n-butyllithium / hexane; diethyl ether / 1 h / 0 - 20 °C 3.2: 16 h / -20 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 2.5 h 1.2: Reflux 2.1: lanthanum(lll) triflate; [3aS-[2(3'aRS,8'aSR),3aα,8aα]]-2,2'-(2,6-pyridinediyl)bis-[3a,8a-dihydro-8H-indeno[1,2-d]oxazole] / acetonitrile / 0.5 h / 20 °C / Schlenk technique; Molecular sieve 2.2: Schlenk technique; Molecular sieve; Inert atmosphere; Cooling |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 2.5 h 1.2: Reflux 2.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: carbonic acid dimethyl ester With sodium hydride In tetrahydrofuran for 2.5h; Stage #2: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one In tetrahydrofuran Reflux; | ||
Stage #1: carbonic acid dimethyl ester With potassium <i>tert</i>-butylate; sodium hydride In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: 5-(tert-butyl)-2,3-dihydro-1H-inden-1-one In tetrahydrofuran at 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 75% 2: 7 %Spectr. | With 3-methylpyridin-2-ylamine; chlorobis(ethylene)rhodium(I) dimer; water; toluene-4-sulfonic acid; 1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In tetrahydrofuran at 150℃; for 72h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride; potassium <i>tert</i>-butylate / tetrahydrofuran / 0.08 h / 20 °C 1.2: 2 h / 20 °C 2.1: zinc(II) oxide / toluene / 12 h / Dean-Stark; Reflux 3.1: C51H61N2O2(1+)*Br(1-); sodium carbonate / toluene; water / 72 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride; potassium <i>tert</i>-butylate / tetrahydrofuran / 0.08 h / 20 °C 1.2: 2 h / 20 °C 2.1: zinc(II) oxide / toluene / 12 h / Dean-Stark; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With chlorobis(ethylene)rhodium(I) dimer; 1,3-bis(4-methoxy-2,6-dimethylphenyl)-4,5-dimethyl-1H-imidazol-2-ylidene; 5-(3,5-bis(trifluoromethyl)phenyl)-3-methylpyridin-2-amine; 1,3-bis(4-methoxy-2,6-dimethylphenyl)-4,5-dimethyl-1H-imidazol-3-ium 4-methylbenzenesulfonate; toluene-4-sulfonic acid In water; toluene at 140℃; for 72h; Sealed tube; Inert atmosphere; |
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