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Chemical Structure| 36626-29-6 Chemical Structure| 36626-29-6

Structure of 36626-29-6

Chemical Structure| 36626-29-6

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Product Details of [ 36626-29-6 ]

CAS No. :36626-29-6
Formula : C21H20ClO2P
M.W : 370.81
SMILES Code : O=C(CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)O.[Cl-]
MDL No. :MFCD00185663
InChI Key :GALLWJZTZYJVSL-UHFFFAOYSA-N
Pubchem ID :10270534

Safety of [ 36626-29-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501

Application In Synthesis of [ 36626-29-6 ]

* 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.

  • Downstream synthetic route of [ 36626-29-6 ]

[ 36626-29-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5779-93-1 ]
  • [ 36626-29-6 ]
  • (3E)-4-(2,3-dimethylphenyl)but-3-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at 0 - 20℃; Briefly, to a solution of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> (4 g, 29.81 mmol, 1.00 equiv) and (2-carboxyethyl)triphenylphosphanium chloride (12.2 g, 32.90 mmol, 1.10 equiv) in 1 : 1 mixture of dry THF/DMSO (100 mL) was added sodium hydride (2.2 g, 64.17 mmol, 2.10 equiv, 70percent) at 0°C. The resulting solution was allowed to stir overnight at room temperature. Water was added and the aqueous layer was adidified to pH 1-2 with concentrated HC1 aqueous, and extracted with ethyl acetate. The combined organic phases were dried over anhydrous a2S04. After filtration and concentration, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether=l/8 to 1/2. This resulted in 2.2 g (38percent) of (E)- 4-(2,3-dimethylphenyl)but-3-enoic acid as a colorless solid. Next, a solution of (E)-4-(2,3- dimethylphenyl)but-3-enoic acid (3.3 g, 17.35 mmol, 1.00 equiv) in methanol (30 mL), palladium carbon (0.5 g) was placed in a 100 mL round bottom flask. Hydrogen was bubbled into the mixture and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the filtrate was concentrated under reduced pressure. This resulted in 3.2 g (95percent) of 4-(2,3-dimethylphenyl)butanoic acid as a white solid. After this, a solution of 4-(2,3-dimethylphenyl)butanoic acid (3.2 g, 16.64 mmol, 1.00 equiv) in TfOH (50 mL) was placed into a 100 mL round bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether=l/6. This resulted in 2.4 g (82percent) of 5,6-dimethyl-3,4-dihydronaphthalen-l(2H)-one as a light yellow solid. Next, a solution of l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazole (1.14 g, 5.75 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) was placed into a 100 mL 3- necked round bottom flask. This was followed by the addition of n-BuLi (2.3 mL, 2.5M) and the reaction mixture was stirred for 1 h at -70 °C. To this was added 5,6-dimethyl-3,4- dihydronaphthalen-l(2H)-one (1 g, 5.74 mmol, 1.00 equiv) at -70 °C. The reaction mixture was warmed to room temperature over a period of 2 hrs. Then, water was added and extracted with EtOAc. The combined organic phases were dried over anhydrous Na2S04. After filtration and concentration, the residue was purified by MPLC. This resulted in 1.5 g (69percent) of 5,6-dimethyl-l-(l-((2-(trimethylsilyl)ethoxy)methyl)-lH-imidazol-2-yl)-l,2,3,4- tetrahydronaphthalen-l-ol as a white solid. LCMS(m/e) 373 (M+H); NMR (300 MHz, CDC13) delta ppm 7.00-7.03 (m, 2H), 6.92 (d, J=7.8 Hz, 1H), 6.66 (d, J=7.8 Hz, 1H), 4.93 (s, 1H), 4.67-4.75 (m, 2H), 3.30-3.40 (m, 1H), 3.08-3.15 (m, 1H), 2.88-2.98 (m, 1H), 2.52-2.68 (m, 1H), 2.27 (s, 3H), 2.20 (s, 3H), 2.02-2.20 (m, 3H), 1.85-2.00 (m, 1H), 0.78-0.85 (m, 2H), -0.02 (s, 9H). Following this, a solution of 5,6-dimethyl-l-(l-((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazol-2-yl)-l,2,3,4-tetrahydronaphthalen-l-ol (250 mg, 0.67 mmol, 1.00 equiv) in dichloromethane (5 mL), trifluoroacetic acid (5 mL) was placed into a 100 mL round bottom flask. The resulting solution was stirred for 3 h at room temperature. The pH value of the solution was adjusted to 8 with sodium bicarbonate. The resulting solution was extracted with dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by MPLC. This resulted in 30 mg (18percent) of l-(lH-imidazol-2-yl)-5,6-dimethyl- 1,2,3,4-tetrahydronaphthalen-l-ol as a yellow solid. LCMS(m/e) 359 (M+H); XH NMR (400 MHz, CDCI3) delta ppm 7.11 (d, J=7.6 Hz, 1H), 7.02-7.12 (m, 3H), 6.78 (d, J=7.6 Hz, 1H), 5.10 (s, 1H), 4.62-4.72 (m, 2H), 3.30-3.42 (m, 1H), 3.07-3.18 (m, 1H), 2.84-2.95 (m, 1H), 2.54- 2.68 (m, 1H), 2.31 (s, 3H), 2.11-2.26 (m, 3H), 1.92-2.01 (m, 1H), 0.83 (t, J=8.4 Hz, 2H), - 0.02 (s, 9H). Finally, a solution of 2-(5,6-dimethyl-3,4-dihydronaphthalen-l-yl)-lH- imidazole (100 mg, 0.45 mmol, 1.00 equiv) in methanol (10 mL), Palladium carbon (20 mg, 10percent) was placed into a 100 mL round bottom flask. Hydrogen was bubbled into the solution and the resulting mixture was stirred for 1 overnight at room temperature. The solids were filtered out and the residue was purified by MPLC. This resulted in 80 mg (78percent) of 2-(5,6- dimethyl-l,2,3,4-tetrahydronaphthalen-l-yl)-lH-imidazole as a white solid. LCMS(m/e) 213 (M+H); NMR (300 MHz, CDC13) delta ppm 7.02-7.15 (m, 2H), 6.86-6.95 (m, 3H), 4.39 (t, J=5.1 Hz, 1H), 2.62-2.75 (m, 2H), 2.20-2.32 (m, 1H), 2.26 (s, 3H), 2.01-2.17 (m, 1H), 1.82- 1.98 (m, 1H), 1.62-1.78 (m, 1H).
38% With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; at 0 - 20℃; Briefly, to a solution of <strong>[5779-93-1]2,3-dimethylbenzaldehyde</strong> (4 g, 29.81 mmol, 1.00 equiv) and (2-carboxyethyl)triphenylphosphanium chloride (12.2 g, 32.90 mmol, 1.10 equiv) in 1:1 mixture of dry THF/DMSO (100 mL) was added sodium hydride (2.2 g, 64.17 mmol, 2.10 equiv, 70percent) at 0° C. The resulting solution was allowed to stir overnight at room temperature. Water was added and the aqueous layer was acidified to pH 1-2 with concentrated HCl aqueous, and extracted with ethyl acetate. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether=1/8 to 1/2. This resulted in 2.2 g (38percent) of (E)-4-(2,3-dimethylphenyl)but-3-enoic acid as a colorless solid. Next, a solution of (E)-4-(2,3-dimethylphenyl)but-3-enoic acid (3.3 g, 17.35 mmol, 1.00 equiv) in methanol (30 mL), palladium carbon (0.5 g) was placed in a 100 mL round bottom flask. Hydrogen was bubbled into the mixture and the resulting solution was stirred overnight at room temperature. The solids were filtered out and the filtrate was concentrated under reduced pressure. This resulted in 3.2 g (95percent) of 4-(2,3-dimethylphenyl)butanoic acid as a white solid. After this, a solution of 4-(2,3-dimethylphenyl)butanoic acid (3.2 g, 16.64 mmol, 1.00 equiv) in TfOH (50 mL) was placed into a 100 mL round bottom flask. The resulting solution was stirred overnight at room temperature. Then, ice-water was added and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether=1/6. This resulted in 2.4 g (82percent) of 5,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one as a light yellow solid. Next, a solution of 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (1.14 g, 5.75 mmol, 1.00 equiv) in tetrahydrofuran (30 mL) was placed into a 100 mL 3-necked round bottom flask. This was followed by the addition of n-BuLi (2.3 mL, 2.5M) and the reaction mixture was stirred for 1 h at ?70° C. To this was added 5,6-dimethyl-3,4-dihydronaphthalen-1(2H)-one (1 g, 5.74 mmol, 1.00 equiv) at ?70° C. The reaction mixture was warmed to room temperature over a period of 2 hrs. Then, water was added and extracted with EtOAc. The combined organic phases were dried over anhydrous Na2SO4. After filtration and concentration, the residue was purified by MPLC. This resulted in 1.5 g (69percent) of 5,6-dimethyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-1,2,3,4-tetrahydronaphthalen-1-ol as a white solid. LCMS (m/e) 373 (M+H); 1H NMR (300 MHz, CDC3) delta ppm 7.00-7.03 (m, 2H), 6.92 (d, J=7.8 Hz, 1H), 6.66 (d, J=7.8 Hz, 1H), 4.93 (s, 1H), 4.67-4.75 (m, 2H), 3.30-3.40 (m, 1H), 3.08-3.15 (m, 1H), 2.88-2.98 (m, 1H), 2.52-2.68 (m, 1H), 2.27 (s, 3H), 2.20 (s, 3H), 2.02-2.20 (m, 3H), 1.85-2.00 (m, 1H), 0.78-0.85 (m, 2H), ?0.02 (s, 9H). Following this, a solution of 5,6-dimethyl-1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-1,2,3,4-tetrahydronaphthalen-1-ol (250 mg, 0.67 mmol, 1.00 equiv) in dichloromethane (5 mL), trifluoroacetic acid (5 mL) was placed into a 100 mL round bottom flask. The resulting solution was stirred for 3 h at room temperature. The pH value of the solution was adjusted to 8 with sodium bicarbonate. The resulting solution was extracted with dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by MPLC. This resulted in 30 mg (18percent) of 1-(1H-imidazol-2-yl)-5,6-dimethyl-1,2,3,4-tetrahydronaphthalen-1-ol as a yellow solid. LCMS (m/e) 359 (M+H); 1H NMR (400 MHz, CDC3) delta ppm 7.11 (d, J=7.6 Hz, 1H), 7.02-7.12 (m, 3H), 6.78 (d, J=7.6 Hz, 1H), 5.10 (s, 1H), 4.62-4.72 (m, 2H), 3.30-3.42 (m, 1H), 3.07-3.18 (m, 1H), 2.84-2.95 (m, 1H), 2.54-2.68 (m, 1H), 2.31 (s, 3H), 2.11-2.26 (m, 3H), 1.92-2.01 (m, 1H), 0.83 (t, J=8.4 Hz, 2H), ?0.02 (s, 9H). Finally, a solution of 2-(5,6-dimethyl-3,4-dihydronaphthalen-1-yl)-1H-imidazole (100 mg, 0.45 mmol, 1.00 equiv) in methanol (10 mL), Palladium carbon (20 mg, 10percent) was placed into a 100 mL round bottom flask. Hydrogen was bubbled into the solution and the resulting mixture was stirred for 1 overnight at room temperature. The solids were filtered out and the residue was purified by MPLC. This resulted in 80 mg (78percent) of 2-(5,6-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl)-1H-imidazole as a white solid. LCMS (m/e) 213 (M+H); 1H NMR (300 MHz, CDC3) delta ppm 7.02-7.15 (m, 2H), 6.86-6.95 (m, 3H), 4.39 (t, J=5.1 Hz, 1H), 2.62-2.75 (m, 2H), 2.20-2.32 (m, 1H), 2.26 (s, 3H), 2.01-2.17 (m, 1H), 1.82-1.98 (m, 1H), 1.62-1.78 (m, 1H).
 

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