* 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.
With hydrazine hydrate; potassium hydroxide In octanol at 135℃; for 1.75 h;
The product was obtained using a Wolff–Kishner reaction to reduce 1-(4-bromophenyl)decan-1-one 7. 1-(4-Bromophenyl)decan-1-one 7 (1.3g, 4.2mmol), hydrazine monohydrate (1.2mL, 16mmol) and KOH (1.8g, 32mmol) were dissolved in 25mL of 1-octanol to yield a green suspension in a two-necked 50mL flask. The reaction mixture was stirred at reflux at 135°C for 2h to give an almost colorless solution. The reaction mixture was then cooled to room temperature and diluted with ether (50mL), washed with 1N aqueous HCl (50mL), 2N aqueous HCl (20mL), brine (2 times, 30mL), dried over MgSO4, filtered, concentrated in vacuo. 1-Octanol was removed by vacuum distillation to yield about 2.7g of the crude product. The product was purified using column chromatography with heptane as eluent. Yield 40percent. Colorless oil. Rf=0.61 (100percent heptane). 1H NMR (500MHz, CDCl3) δ 7.37 (d, J=8.3, 2H), 7.03 (d, J=8.1, 2H), 2.54 (t, J=7.7, 2H), 1.60–1.54 (m, 2H), 1.28–1.25 (m, 14H), 0.88 (t, J=6.8, 3H).13C NMR (50MHz, CDCl3) δ 142.05, 131.46, 130.37, 119.47, 35.59, 32.14, 31.56, 29.85, 29.82, 29.71, 29.57, 29.43, 22.93, 14.34. MS (APPI): m/z 296.2 [M+].
Reference：
[1] Macromolecules, 2010, vol. 43, # 19, p. 8063 - 8070
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 2, p. 541 - 548
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7763 - 7778
[4] Journal of Materials Chemistry, 2003, vol. 13, # 1, p. 50 - 55
[5] Molecular Crystals and Liquid Crystals, 2003, vol. 396, p. 241 - 250
2
[ 30089-00-0 ]
[ 1746-28-7 ]
[ 106418-67-1 ]
Yield
Reaction Conditions
Operation in experiment
97 mg
With [((Me)NN2)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide In 1,4-dioxane; isopropyl alcohol at 80℃; for 24 h; Inert atmosphere
General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 molpercent), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 μL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 °C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2).
Except that 4-decylaniline was used in place of 4-pentylaniline used in Example 1 (a), the operation was performed in the same manner as in Example 1 to obtain 48.4 g (38%) of 4-decylbromobenzene. b.p. 136-141 C./0.4 mmHg
(c) Synthesis of STR39 A reaction vessel was charged with 0.35 g of magnesium powder and a small piece of iodine. To this mixture was added a small portion of a solution of 4 g of 4-decylbromobenzene obtained in (b) above in 10 ml of THF, whereupon foaming occurred to initiate the reaction. The remainderof the THF solution mentioned above was then added dropwise with stirring in such a manner that the resultant mixture was kept refluxed.
19
[ 7758-89-6 ]
[ 112-29-8 ]
[ 106-37-6 ]
[ 106418-67-1 ]
Yield
Reaction Conditions
Operation in experiment
With N,N,N,N,-tetramethylethylenediamine; iodine; In tetrahydrofuran; nitrogen; benzene;
1 Synthesis of 4-Decylbromobenzene: In a reaction flask were charged 10.2 g of metallic magnesium, 100 ml of THF, and a small amount of iodine in a nitrogen stream, and a part of 500 ml of a THF solution containing 100 g of 1,4-dibromobenzene was added thereto dropwise to initiate reaction. Then, the rest of the solution was added dropwise at 25 to 30 C. over a 2-hour period, and the mixture was allowed to react at 40 C. for 1 hour, followed by cooling to prepare a Grignard reagent. Separately, 187 g of decyl bromide, 500 ml of benzene, 98.3 g of N,N,N',N'-tetramethylethylenediamine, and 2.1 g of copper (I) chloride were put in a reaction flask, and the atmosphere was displaced with nitrogen. The mixture was heated to 50 C., and the above prepared Grignard reagent was added thereto dropwise at that temperature over 30 minutes. The reaction mixture was allowed to react for 24 hours, cooled, and poured into a saturated aqueous ammonium solution, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate to recover 107 g of a crude product. The crude product was distilled in a Claisen flask equipped with a Vigreaux tube cylinder to obtain 43.7 g of the title compound.
With iodine; magnesium; In tetrahydrofuran; nitrogen; ethyl acetate; toluene;
3 Synthesis of 2-Benzyloxy-5-(4-decylphenyl)-pyridine: In a reaction flask were charged 2.17 g of magnesium, 50 ml of THF, and a small amount of iodine in a nitrogen stream. A part of a solution of 26.8 g of 4-decylbromobenzene in 134 ml of THF was added thereto dropwise to initiate reaction. The rest of the solution was added thereto dropwise at 35 to 40 C. over 1 hour, and the mixture was allowed to react at that temperature for 2 hours, followed by cooling to prepare a Grignard reagent. In a reaction flask previously purged with nitrogen were charged 15.2 g of 2-benzyloxy-5-chloropyridine, 150 ml of THF, and 2.68 g of Ni(Ph2 P(CH2)3 PPh2)Cl2, and the above prepared Grignard reagent was added thereto dropwise over a 20-minute period. After the addition, the reaction was further continued at the same temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with toluene. The organic layer was separated by filtration, and the solvent was removed therefrom by evaporation to give 37.18 g of a crude product. Purification by column chromatography using 450 g of silica gel and a 5:1 (by volume) mixture of toluene and ethyl acetate gave 19.9 g of the title compound.
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; In acetonitrile; at 120℃; for 35h;Inert atmosphere; Microwave irradiation;
Into a dried 10-20mL microwave vial, PdCl2(PPh3) (52mg, 74mumol), CuI (18mg, 95mumol), and PPh3 (80mg, 0.30mmol) were suspended in CH3CN (2mL) under nitrogen atmosphere. Subsequently, <strong>[106418-67-1]1-bromo-4-decylbenzene</strong> 8 (0.46g, 1.5mmol), diethyl amine (Et2NH) (2.4mL, 23mmol), and trimethylsilyl acetylene (TMSA) (0.24mL, 1.7mmol), were added to the mixture. The mixture was heated at 120C for 35min via microwave irradiation (95W). The reaction mixture was diluted with EtOAc (50mL) and washed with water (3×50mL). The water layer was washed with EtOAc (2×50mL). The combined organic phases were extracted with brine (1×50mL) and dried over Mg2SO4. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography with heptane as eluent. Yield 65%. Brown oil. Rf=0.41 (100% heptane). 1H NMR (500MHz, CDCl3) delta 7.37 (d, J=8.0, 2H), 7.10 (d, J=7.9, 2H), 2.58 (t, J=7.6, 2H), 1.58-1.54 (m, 2H), 1.28-1.25 (m, 14H), 0.88 (t, J=6.8, 3H), 0.24 (s, 9H);13C NMR (50MHz, CDCl3) delta 143.89, 132.08, 128.52, 120.44, 105.63, 93.45, 36.11, 32.12, 31.42, 29.82, 29.69 (2C), 29.55, 29.42, 22.91, 14.34, 0.26. MS (APPI): m/z 314.2 [M+].
With [((Me)NN2)NiCl]; isopropyl alcohol; sodium iodide; sodium hydroxide; In 1,4-dioxane; isopropyl alcohol; at 80℃; for 24h;Inert atmosphere;
General procedure: To a solution of NaOH (32 mg, 0.8 mmol, 1.6 equiv), catalyst 1 (8.4mg, 0.025 mmol, 5 mol%), NaI (37 mg, 0.25 mmol, 0.5 equiv), and i-PrOH (76 muL, 1 mmol, 2 equiv) in dry 1,4-dioxane (2.4 mL), were added alkyl halide (0.5 mmol) and the alkyl-(9-BBN) (1.6 mL, 0.8mmol, 1.6 equiv) under a N2 atmosphere. The mixture was stirred at 80 C for 24 h. The solution was diluted in Et2O (10 mL), filtered on a short pad of silica, washed with Et2O (3 × 10 mL), and concentrated to dryness under reduced pressure. The residue was purified with a flash purification system to give the coupling product (Tables 1 and 2).
With caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 10h;Schlenk technique;
General procedure: A mixture of the aryl halide (1.0 mmol), K4Fe(CN)6 (0.22 mmol), Cs2CO3 (1.0 mmol), Pd-zeolite (0.025 mmol Pd) and 5 mL of solvent (DMF) was placed in a Schlenk tube (25 mL), and was vigorously stirred for 10 h at 130 C. Upon completion, the mixture was cooled to room temperature, and diluted with ether and water. Organic layer was washed with brine, dried over MgSO4, filtered and evaporated under reduced pressure using rotary evaporator to give the crude product. The residue was purified by recrystallisation using ethanol and water. The purity of the compounds was checked by 1H NMR and yields are based on aryl halide. All the products are known and the spectroscopic data (FT-IR and NMR) and melting points were consistent with those reported in the literature.4-19,38,39
A solution of <strong>[106418-67-1]1-bromo-4-decylbenzene</strong> (11.9 g, 40 mmol) in dehydrated tetrahydrofuran (200 mL) was cooled to -70 C. and a 1.6 M hexane solution of n-BuLi (32.5 mL, 52 mmol) was added dropwise. After stirring for 1 hour, pinacol isopropoxyboronic acid (9.7 g, 52 mmol) was added and the mixture was gradually warmed to room temperature with stirring. Water and toluene were added, the organic layer was separated, sodium sulfate was added and dried, and the solvent was distilled off with an evaporator. The resulting oil was purified on a silica gel column using hexane / ethyl acetate (10/1) as a developing solvent,4-decylphenylboronic acid pinacol ester was obtained as a colorless oil (yield: 9.8 g, yield 71.1%).
It was added in dry nitrogen and continued through reactor 4-n-decyl dibromobenzene 4.41g (14.84mmol)And dried tetrahydrofuran 100ml, the solution was cooled to -78 , was added n-butyllithium in n-hexane21.32ml (35.2mmol), allowed to warm to room temperature and stirred for 2 hours. Mixture was recooled to -78 , was addedIsopropyl pinacolato boronate 5ml (37.2mmol), was slowly warmed to room temperature and stirred for 12 hours. With BThe reaction mixture was extracted with ether, the organic phase was collected, washed with brine, dried over anhydrous sodium sulfate, and the solvent by rotary evaporation,To give a pale yellow oil by column chromatography (petroleum ether) to give the crude product as a colorless oily liquid 10 (4.24g),Yield 83%.
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