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[ CAS No. 28547-33-3 ]

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2D
Chemical Structure| 28547-33-3
Chemical Structure| 28547-33-3
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CAS No. :28547-33-3MDL No. :MFCD11504951
Formula : C13H17ClO Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :224.73Pubchem ID :-
Synonyms :

Computed Properties of [ 28547-33-3 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 28547-33-3 ]

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Precautionary Statements:UN#:
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Application In Synthesis of [ 28547-33-3 ]

  • Downstream synthetic route of [ 28547-33-3 ]

[ 28547-33-3 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 28547-33-3 ]
  • [ 4600-86-6 ]
YieldReaction ConditionsOperation 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.

Reference: [1]Current Patent Assignee: JOHNSON & JOHNSON INC - WO2010/59393, 2010, A1 Location in patent: Page/Page column 125
[2]Boberg, Friedrich; Deters, Karin; Schulz, Juergen; Torges, Karl-Franz [Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 91, # 1-4, p. 69 - 80]
[3]Current Patent Assignee: ABBVIE INC - US2018/194762, 2018, A1 Location in patent: Paragraph 0849
[4]Hannig [Pharmazie, 1965, vol. 20, # 12, p. 762 - 763]
[5]Gomtsyan, Arthur; Bayburt, Erol K.; Schmidt, Robert G.; Surowy, Carol S.; Honore, Prisca; Marsh, Kennan C.; Hannick, Steven M.; McDonald, Heath A.; Wetter, Jill M.; Sullivan, James P.; Jarvis, Michael F.; Faltynek, Connie R.; Lee, Chih-Hung [Journal of Medicinal Chemistry, 2008, vol. 51, # 3, p. 392 - 395]
[6]Current Patent Assignee: ROCHE HOLDING AG - WO2009/98144, 2009, A1 Location in patent: Page/Page column 77-78
[7]Current Patent Assignee: ROCHE HOLDING AG - US2010/4231, 2010, A1 Location in patent: Page/Page column 73
[8]Current Patent Assignee: ROCHE HOLDING AG - US2010/222325, 2010, A1 Location in patent: Page/Page column 99-101
[9]Current Patent Assignee: ABBVIE INC - US2007/99954, 2007, A1 Location in patent: Page/Page column 28
[10]Current Patent Assignee: Gruenenthal Pharma GmbH & Co. Kommanditgesellschaft - WO2012/62463, 2012, A1 Location in patent: Page/Page column 76-77
[11]Location in patent: experimental part Nishida, Jun-Ichi; Deno, Hironori; Ichimura, Satoru; Nakagawa, Tomohiro; Yamashita, Yoshiro [Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4483 - 4490]
[12]Lukin, Kirill; Hsu, Margaret C.; Chambournier, Gilles; Kotecki, Brian; Venkatramani; Leanna [Organic Process Research and Development, 2007, vol. 11, # 3, p. 578 - 584]
[13]Current Patent Assignee: ABBVIE INC - US2004/254188, 2004, A1 Location in patent: Page 14
  • 2
  • [ 28547-33-3 ]
  • [ 1178884-68-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / 20 °C 2: sodium azide / dichloromethane; methanesulfonic acid / 2 h / 0 - 20 °C / Inert atmosphere
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