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Chemical Structure| 1883-32-5
Chemical Structure| 1883-32-5
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Product Details of [ 1883-32-5 ]

CAS No. :1883-32-5 MDL No. :MFCD00004729
Formula : C14H14O Boiling Point : -
Linear Structure Formula :- InChI Key :NYLOEXLAXYHOHH-UHFFFAOYSA-N
M.W : 198.26 Pubchem ID :74662
Synonyms :

Safety of [ 1883-32-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1883-32-5 ]

* 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 [ 1883-32-5 ]

[ 1883-32-5 ] Synthesis Path-Downstream   1~39

  • 3
  • [ 947-91-1 ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
96%Chromat. With formic acid; iron(II) tetrafluoroborate hexahydrate; tris(2-diphenylphosphinoethyl)phosphine; In tetrahydrofuran; at 60℃; for 2h;Schlenk technique; Inert atmosphere; General procedure: Fe(BF4)2·6H2O (0.7 mg; 0.002 mmol) and tris[2-(diphenyl-phosphino)-ethyl]phosphine [P(CH2CH2PPh2)3; tetraphos] (1.4 mg; 0.002 mmol) are placed in a Schlenk-tube under argon atmosphere. 1 mL dry tetrahydrofurane is added and the purple solution is stirred for 2 min. Cinnamaldehyde (63 muL; 0.5 mmol) and 100 muL n-hexadecane as an internal GC-standard are injected and a sample is taken for GC-analysis. The solution is heated to 60 C and the reaction starts by addition of 1.1 equiv formic acid (22 muL; 0.55 mmol). After 2 h, a second sample is taken for GC-analysis and conversion and yield are determined by comparison with authentic samples. For the isolation, the reaction is scaled up by a factor of 20. When the reaction is completed, the reaction solution is diluted with a mixture of n-hexane and ethyl acetate (3:1), filtered through a plug of silica and the solvent removed in vacuum.
  • 4
  • [ 3468-99-3 ]
  • [ 612-00-0 ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
With copper oxide-chromium oxide; hydrogen at 200℃;
  • 6
  • [ 117-34-0 ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
92% In the inert gas N2 atmosphere, after dehydration and deoxidation treatment to the reaction bottle after adding diphenyl acetic acid (105.8 mg, 0.5 mmol, gun for adding [...] borane (289 mul, 2 mmol), reacting at room temperature 12 hours, the reaction out of the glove box, in order to have three methoxybenzene (83.84 mg, 0.5 mmol) as the internal standard, CDCl3 for dissolving, stirring 10 minutes, sampling, with nuclear magnetic resonance. Calculated 1 H and the yield is 99%. The product of nuclear magnetic data: The residue is added to the sample in 1 g silica gel, in order to 3 ml methanol as a solvent, 50 C lower reaction 3 h, the borate further hydrolysis alcohol, after the reaction, extracted with ethyl acetate three times, the combined organic layer, dried with anhydrous sodium sulfate, the solvent is removed under reduced pressure, through the silica gel (100 - 200 mesh) column chromatography purification, ethyl acetate/hexane (1:5) mixture as the eluent, to obtain the pure primary alcohol, separation and the yield is 92%.
86% With 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate); In toluene; at 80℃; for 16h;sealed tube; General procedure: In a sealed tube, 29 mg Cu(OTf)2 (0.08 mmol, 8 mol %) and 0.7 mL TMDS (537 mg, 4 mmol, 8 Si-H mol/mol substrate) were introduced to a solution of aliphatic carboxylic acid (1 mmol) in 1.5 mL toluene. After stirring 16 h at 80 C, the reaction mixture was cooled to room temperature and quenched with 4 mL H2O. The organic layer was extracted with CH2Cl2, dried with anhydrous MgSO4, and evaporated under reduced pressure. The crude was purified by silica gel column chromatography to obtain the alcohol.
  • 9
  • [ 67-56-1 ]
  • [ 530-48-3 ]
  • [ 612-00-0 ]
  • [ 1483-64-3 ]
  • [ 1883-32-5 ]
  • [ 20017-67-8 ]
  • [ 39153-68-9 ]
  • [ 74421-26-4 ]
  • 10
  • [ 67-56-1 ]
  • [ 947-40-0 ]
  • [ 612-00-0 ]
  • [ 1883-32-5 ]
  • [ 20017-67-8 ]
  • [ 4801-14-3 ]
  • [ 74421-26-4 ]
  • 11
  • [ 3469-00-9 ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
92.4% With diisobutylaluminium hydride; In dichloromethane; toluene; at -30 - 25℃; for 12h; (2) Preparation of 2,2-diphenylethanol To a 500 mL three-opening flask was slowly added a solution of diisobutylaluminum hydride in toluene (282 mL, 1 mol/L) at -30 C. After stirring, to the resulting mixture was slowly added a solution of methyl 2,2-diphenylacetate (21 g, 92.8 mmol) in dichloromethane dropwisely. After the completion of dropwise addition, the reaction was conducted at 25 C. for 12 hours. After the completion of reaction monitored by TLC, to the resulting mixture was slowly added methanol (10 mL), dichloromethane (100 mL) and an aqueous sodium hydroxide solution (100 mL, 1 mol/L) at -20 C. After the completion of reaction, to the reaction solution was added dichloromethane for extraction. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce 2,2-diphenyl ethanol (17 g) in a yield of 92.4%.
92.4% With diisobutylaluminium hydride; In dichloromethane; toluene; at 25℃; for 12h; (2) Preparation of 2,2-diphenylethanol To a 500mL three-opening flask was slowly added a solution of diisobutylaluminum hydride in toluene (282mL, 1mol/L) at -30C. After stirring, to the resulting mixture was slowly added a solution of methyl 2,2-diphenylacetate (21g, 92.8mmol) in dichloromethane dropwisely. After the completion of dropwise addition, the reaction was conducted at 25 C for 12 hours. After the completion of reaction monitored by TLC, to the resulting mixture was slowly added methanol (10mL), dichloromethane (100mL) and an aqueous sodium hydroxide solution (100mL, 1mol/L) at -20C. After the completion of reaction, to the reaction solution was added dichloromethane for extraction. The organic phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to remove the solvent to produce 2,2-diphenyl ethanol (17 g) in a yield of 92.4 %.
  • 13
  • [ 1883-32-5 ]
  • [ 75-86-5 ]
  • [ 2286-54-6 ]
  • 15
  • [ 108-30-5 ]
  • [ 1883-32-5 ]
  • 2,2-diphenylethyl monosuccinate [ No CAS ]
  • 16
  • [ 1883-32-5 ]
  • [ 40231-75-2 ]
  • 17
  • [ 937-32-6 ]
  • [ 1883-32-5 ]
  • 2,2-diphenylethyl 4-nitrobenzenesulfenate [ No CAS ]
  • 18
  • [ 914300-11-1 ]
  • [ 1883-32-5 ]
  • 19
  • [ 3871-20-3 ]
  • [ 1883-32-5 ]
  • [ 906072-79-5 ]
  • 20
  • [ 56-91-7 ]
  • [ 1883-32-5 ]
  • 4-[2,2-(diphenyl)ethoxycarbamoyl-methyl]benzoic acid [ No CAS ]
  • [ 110-54-3 ]
YieldReaction ConditionsOperation in experiment
90% With CDI; In tetrahydrofuran; sodium hydroxide; A. A mixture of 2,2-diphenylethanol (6 g, 30 mmoles), CDI (4.9 g, 30 mmoles) in THF (30 ml) was stirred at room temperature for 2 hours, then a solution of 4-aminomethylbenzoic acid (4.6 g, 30 mmoles) in 1N sodium hydroxide (30 ml) was added thereto. The reaction mixture was stirred at room temperature for 3 hours, then acidified with HCl, THF was evaporated in the cold, then the aqueous solution was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated off. The resulting crude was treated with warm n-hexane and filtered to give 10 g of 4-[2,2-(diphenyl)ethoxycarbamoyl-methyl]benzoic acid (90% yield); m.p.=102-105 C. 1 H-NMR d 12.7 (s, 1H, exchange with D2 O), 7.91 (d, 2H), 7.78 (t, 1H), 7.50-7.20 (m, 12H), 4.61 (d, 2H), 4.38 (t, 1H), 4.23 (d, 2H).
  • 21
  • [ 1114967-79-1 ]
  • (R)-2-amino-2-((S)-2-oxocyclohexyl)acetic acid tetrafluoroborate [ No CAS ]
  • [ 1883-32-5 ]
  • 22
  • [ 1114967-82-6 ]
  • (2R,3S)-2-amino-3-methyl-4-oxopentanoic acid tetrafluoroborate [ No CAS ]
  • [ 1883-32-5 ]
  • 23
  • [ 1114967-85-9 ]
  • (2R,3S)-2-amino-3-methyl-4-oxohexanoic acid tetrafluoroborate [ No CAS ]
  • [ 1883-32-5 ]
  • 24
  • [ 1883-32-5 ]
  • [ 874-60-2 ]
  • [ 856374-18-0 ]
  • 25
  • [ 1883-32-5 ]
  • [ 98631-72-2 ]
  • C27H24O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
210 mg With organic base; In dichloromethane; at 20℃; for 12h; General procedure: A mixture of diacetylcaffeic acid,19 5 mL of thionylchloride, and two drops of DMF was heated at reflux for 4 h. The excess of thionyl chloride was removed on a Rotovap, and the residue was dissolved in 4 mL of dry dichloromethane. To this solution was slowly added 1 mL of pyridine and the appropriate alcohol derivative (1.2 equiv). The resulting mixture was stirred overnight at room temperature. After removal of solvents, the residue was dissolved in ethyl acetate (50 mL), the organic extract was washed with water (2 Chi 20 mL), brine (2 Chi 20 mL), and then dried over MgSO4. The residue was then puried by silica gel circular chromatography (Chromatotrons, Model 7924, Harrison Research) to afford the required ester derivative. 5.1.2.20. Compound 20: procedure 2. Ester 19 (210 mg, 69%) was obtained after silica gel circular chromatography (5-40% EtOAc-hexane) as a yellow oil; 1H NMR (400 MHz, CDCl3, 25 C) delta (ppm): 7.55 (d, J = 15.97 Hz, 1H, CHCar), 7.38-7.21 (m, 13H, Har), 6.31 (d, J = 15.97 Hz, 1H, CHCO), 4.78 (d, J = 7.56 Hz, 2H, CH2-CH(Ph)2), 4.46 (t, J = 7.52 Hz, 1H, CH2CH(Ph)2), 2.32 (s, 6H, 2OAc); 13C NMR (101 MHz, CDCl3, 25 C) delta (ppm): 168.09, 168.00, 166.46, 143.49, 143.05, 142.40, 141.11, 133.22, 128.62, 128.23, 126.85, 126.49, 123.90, 122.70, 119.05, 66.90, 49.90, 20.67, 20.63; HRMS m/z calcd for C27H24O6+(H+): 445.1646; found: 445.1628.
  • 26
  • [ 1883-32-5 ]
  • [ 124-63-0 ]
  • [ 205390-22-3 ]
YieldReaction ConditionsOperation in experiment
96.78% (3) Preparation of 2,2-diphenylethyl methanesulfonate In a 500 mL three-opening flask, <strong>[1883-32-5]2,2-diphenyl ethanol</strong> (17 g, 86 mmol) was dissolved in 170 mL dichloromethane. To the flask was added triethylamine (13.03 g, 129 mmol). The resulting mixture was stirred at 0 C. for half an hour. To the resulting mixture was slowly added MsCl (11.92 g, 104 mmol) dropwisely. The reaction was conducted at 25 C. After the completion of reaction monitored by TLC, the reaction solution was washed with water thrice. The organic phase was dried over anhydrous sodium sulfate and evaporated to remove the solvent to produce 2,2-diphenylethyl methanesulfonate (23 g) in a yield of 96.78%.
96.78% With triethylamine; In dichloromethane; at 0 - 25℃; for 0.5h; (3) Preparation of 2,2-diphenylethyl methanesulfonate In a 500mL three-opening flask, <strong>[1883-32-5]2,2-diphenyl ethanol</strong> (17g, 86mmol) was dissolved in 170mL dichloromethane. To the flask was added triethylamine (13.03g, 129mmol). The resulting mixture was stirred at 0C for half an hour. To the resulting mixture was slowly added MsCl (11.92g, 104mmol) dropwisely. The reaction was conducted at 25C. After the completion of reaction monitored by TLC, the reaction solution was washed with water thrice. The organic phase was dried over anhydrous sodium sulfate and evaporated to remove the solvent to produce 2,2-diphenylethyl methanesulfonate (23g) in a yield of 96.78 %.
  • 27
  • [ 32315-10-9 ]
  • [ 1883-32-5 ]
  • 2,2-diphenylethyl chloroformate [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Substrates, 1 and 2, were synthesized by the same method of 2-adamantyl chloroformate. The triphosgene treated in toluene at 0-4 C (ice bath) for 20 min. The mixture of 2-phenylethanol or 2,2-diphenylethanol with pyridine was prepared in toluene at room temperature. Then the latter mixture was added to the former solution slowly. After the stirring for 1 h, the organic mixture was washed with water and dried by magnesium sulfate. The solvent was removed by the evaporation, the colorless oil (1) or white solid (2) was obtained as a crude product. The substrate 1 was purified from vacuum distillation (120 C and 18 torr) and the substrate 2 was recrystallized by using ligroin. Solvents were purified as described previously.
  • 28
  • [ 1883-32-5 ]
  • [ 1311393-11-9 ]
  • 5-(2,2-diphenylethoxy)-2-[4-(trifluoromethyl)benzyl]oxy}benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
20.1% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃;Inert atmosphere; General procedure: In a three-neck round-bottom flask with argon-inlet, septum, reflux condenser,magnetic stirring bar and ice bath E1, E2 and TPP were solved in THF underargon-athmosphere and cooled to 0C. The diisopropylazodicarboxylate (ADDP for24a, both either diluted in a few ml of THF) was added within 5 to 10 minutesvia septum. After completion of reaction (17-24h) the solvent was evaporated,the residue worked up by coloumn chromatography and the product furtherpurified by recrystallization (hexane/ethylacetate).
  • 29
  • [ 1576-43-8 ]
  • [ 1883-32-5 ]
  • 4-(2',2'-diphenylethoxy)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0℃; for 0.416667h;Sonication; General procedure: A solution of 4-hydroxybenzenesulfonamide (1.0g, 1.0equiv), alcohol (1.0equiv) and triphenylphosphine (1.0equiv) in dry THF (20ml) was sonicated at 0C for 5min (scheme C). Then DIAD (1.1equiv) was added drop-wise and the orange solution sonicated at the same temperature for 20min, quenched with H2O (20ml) and extracted with ethyl acetate (3×15ml). The combined organic layers were washed with H2O (3×20ml), dried over Na2SO4, filtered and concentrated in vacuo to give a sticky residue that was purified by silica gel column chromatography eluting with 50% ethyl acetate/n-hexane 50% v/v to and the white solid obtained was recrystallized from IPA.Synthesis of 4-(2',2'-diphenylethoxy)benzenesulfonamide (2n).fx17The synthesis was carried out according to the general procedure in scheme C to afford the desired product as a yellow solid. 4-(2',2'-Diphenylethoxy)benzenesulfonamide 2n: 53% yield; silica gel TLC Rf 0.44 (Ethyl acetate/n-hexane 50% v/v); mp 176 C; deltaH (400 MHz, DMSO-d6) 4.56 (1H, t, J 7.2, 2'-H), 4.68 (2H, d, J 7.2, 1'-H2), 7.12 (2H, d, J 8.8, Ar-H), 7.23 (2H, s, exchange with D2O, SO2NH2), 7.26 (2H, d, J 8.8, Ar-H), 7.43 (8H, m, Ar-H), 7.76 (2H, d, J 8.8, 2 * 2-H); deltaC (100 MHz, DMSO-d6) 161.7, 142.7, 137.2, 129.4, 129.0, 128.5, 127.5, 115.6, 71.2, 50.6; m/z (ESI positive) 354.11 [M+H]+.
  • 30
  • [ 1883-32-5 ]
  • [ 2873-29-2 ]
  • 2,2-diphenylethyl-4,6-di-O-acetyl-2,3-dideoxy-β-D-erythrohex-2-enopyranoside [ No CAS ]
  • 2,2-diphenylethyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine(I) bromide; In dichloromethane; toluene; at 0 - 20℃; for 1h;Inert atmosphere; General procedure: A mixture of 3,4,6-tri-O-acetyl-D-glucal 1 (50.0 mg, 0.184 mmol) and alcohol (0.193 mmol) was dissolved in dry-CH2Cl2 : dry-toluene (125 : 200 muL) under gas-nitrogen. The solution was cooled to 0 C, then 0.5 M IBr in CH2Cl2 (20 mol%, 75 L) was added slowly. The stirring was continued at 0-20 C for 1-10 h. After TLC showed the completed conversion, the reaction mixture was quenched carefully with cooled aq.Na2S2O3 (20 mL) and washed with satd aq. NaHCO3 (20 mL), and extracted with EtOAc (3×20 mL). The combined organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4, and then concentrated under reduced pressure. The residues were purified by silica gel column chromatography (EtOAc/n-hexane) to give the 2,3-unsaturated-O-glycoside products 2a-2t in good to high yields (71-99%). In most cases, a mixture of alpha and beta-anomers of glycoside 2 was obtained. The ratio of the isomers was determined by comparison of the integration values of the peaks in 1H NMR analysis. The alpha-configuration was characterized from the position of anomeric proton which appears in an up fieldposition compared to -anomer in most cases. The beta-isomers was not separated but characterized compared with the literature data of the mixture. Spectral data of pure alpha-isomers are as followed.
  • 31
  • [ 1883-32-5 ]
  • [ 935-79-5 ]
  • (1R,6S)-6-(benzhydrylmethoxycarbonyl)-3-cyclohexenecarboxylic Acid [ No CAS ]
  • (1S,6R)-6-(benzhydrylmethoxycarbonyl)-3-cyclohexenecarboxylic Acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 6h; General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4.
  • 32
  • [ 1883-32-5 ]
  • [ 2746-19-2 ]
  • (1R,2R,5S,6S)-6-(2,2-diphenylethoxy)carbonyl-2,5-methylene-3-cyclohexenecarboxylic acid [ No CAS ]
  • (1S,2S,5R,6R)-6-(2,2-diphenylethoxy)carbonyl-2,5-methylene-3-cyclohexenecarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 12h; General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4.
  • 33
  • [ 4295-92-5 ]
  • [ 1883-32-5 ]
  • (2S,4R)-1-benzhydrylmethyl hydrogen 2,4-dimethylpentandioate [ No CAS ]
  • (2R,4S)-1-benzhydrylmethyl hydrogen 2,4-dimethylpentandioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 15h; General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4.
  • 34
  • [ 4160-80-9 ]
  • [ 1883-32-5 ]
  • (S)-1-benzhydrylmethyl hydrogen 3-phenylpentandioate [ No CAS ]
  • (R)-1-benzhydrylmethyl hydrogen 3-phenylpentandioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 16h; General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4.
  • 35
  • [ 4166-53-4 ]
  • [ 1883-32-5 ]
  • (S)-1-benzhydrylmethyl hydrogen 3-methylpentandioate [ No CAS ]
  • (R)-1-benzhydrylmethyl hydrogen 3-methylpentandioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (R)-3,3?-bis(2,4,6-triisopropylphenyl)-6,6?-dinitro-1,1?-binaphthylphosphate; In chloroform; at 20℃; for 6h; General procedure: To a mixture of 2 (0.10 mmol), catalyst 1 (5mol%), and alcohol 3 (0.11 mmol), was added CHCl3 (0.25 mL) at rt. The mixture was stirred at rt for indicated time in the tables and diluted with Et2O (5 mL). The organic layer was extracted with saturated aq. Na2CO3 (3 mL),and the aqueous layer was acidified with 6 N HCl. The aqueous layer was extracted with Et2O (5 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography to afford the desired product 4.
  • 36
  • [ 1883-32-5 ]
  • [ 65-85-0 ]
  • [ 111583-55-2 ]
  • 37
  • [ 86-29-3 ]
  • [ 1883-32-5 ]
  • 38
  • 2-(2,2-diphenylethoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 1883-32-5 ]
YieldReaction ConditionsOperation in experiment
91%Spectr. With methanol; silica gel; at 50℃; for 2.25h; In an inert gas atmosphere,To the reaction flask after dehydration and deoxidation, diphenylacetic acid (105.8 mg,0.5 mmol, a pinacol borane (289 muL, 2 mmol) was added with a pipette, and finally a solution of 2,6-dimethylanilinium lithium (0.8 mol%) in tetrahydrofuran was added and reacted at room temperature for 75 minutes. The reaction solution is exposed to air, and the solvent is removed to obtain a product borate.The 1H yield was calculated to be 99%.Add to the system for removing the solvent after the hydroboration reaction1 g of silica gel, 3 mL of methanol, and reacted at 50 C for 135 minutes.The organic layer was combined and dried over anhydrous sodium sulfate.The solvent was removed under reduced pressure and purified by silica gel (100-200 mesh) column chromatography.Using ethyl acetate/hexane (1:5 by volume) mixture as eluent,An alcohol compound is obtained. The nuclear magnetic yield was 91%.
91%Spectr. With silica gel; In methanol; at 50℃; for 2h; In an inert gas atmosphere,Diphenylacetic acid (105.8 mg, 0.5 mmol) was added to the reaction vial after dehydration and deoxygenation, and pinacol borane (289 muL, 2 mmol) was added using a pipette.Finally, a solution of n-butyllithium (0.5 mol%) in tetrahydrofuran is added.The reaction was carried out for 45 minutes at room temperature, and the reaction solution was exposed to air to remove the solvent to obtain the product boric acid.The ester was calculated to have a 1H yield of 99%. Nuclear magnetic data of the product:1H NMR (400 MHz, CDCl3): delta 7.13-7.32 (m, 10H, ArCH), 4.41 (d, 2H, CH2, OCH2), 4.24 (t, 1H, CH), 1.23 (s,24H, CH3, pinBOBpin ), 1.12 (s, 12H, CH3, OBpin).To the system after removing the solvent from the hydroboration reaction, 1 g of silica gel and 3 mL of methanol were added, and the reaction was carried out at 50 C for 2 hours. After the reaction was completed, the mixture was extracted three times with ethyl acetate.After drying, the solvent was removed under reduced pressure and purified by silica gel (100-200 mesh) column eluting with ethyl acetate/hexane (1:5 by volume) as eluent.The nuclear magnetic yield was 91%. Nuclear magnetic data of the product: 1H NMR (400 MHz,CDCl3): delta 7.20-7.31 (m, 10H, ArCH), 4.19 (t, 1H, CH), 4.13 (d, 2H, CH2), 1.64-1.70 (t, 1H, OH).
  • 39
  • potassium (2,2-diphenylethyl)trifluoroborate [ No CAS ]
  • [ 1883-32-5 ]
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Similarity: 0.92

Alcohols

Chemical Structure| 37778-99-7

[ 37778-99-7 ]

(S)-2-Phenylpropan-1-ol

Similarity: 0.96

Chemical Structure| 1123-85-9

[ 1123-85-9 ]

2-Phenylpropan-1-ol

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Chemical Structure| 67634-10-0

[ 67634-10-0 ]

p-Isopropyl-beta-methylphenethyl alcohol

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Chemical Structure| 5464-86-8

[ 5464-86-8 ]

2,2-Diphenylpropane-1,3-diol

Similarity: 0.92

Chemical Structure| 2173-69-5

[ 2173-69-5 ]

2-Methyl-2-phenyl-1-propanol

Similarity: 0.92