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CAS No. : | 18531-94-7 | MDL No. : | MFCD00004068 |
Formula : | C20H14O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PPTXVXKCQZKFBN-UHFFFAOYSA-N |
M.W : | 286.32 | Pubchem ID : | 11762 |
Synonyms : |
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Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P301+P310+P330-P302+P352-P305+P351+P338 | UN#: | 2811 |
Hazard Statements: | H301-H315-H319 | Packing Group: | Ⅲ |
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 |
---|---|---|
26% | General procedure: (R,R)-N,N?-dibenzyl-1,2-cyclohexanediamine (1.06 g, 3.6 mmol) and NEt3 (1.50 mL, 10.8 mmol) were dissolved in 10 mL of toluene.PCl3 (0.40 mL, 4.6 mmol) dissolved in 5 mL of toluene was addeddrop wise at 0 C. The mixture was allowed to warm up to roomtemperature and was stirred for 2 h. The formation of the chlorodiazaphospholidinewas monitored by 31P NMR spectroscopy(d 174.5 ppm) being complete after this period. The solvent andthe excess of PCl3 were thoroughly removed under reduced pressureto afford a viscous oil. This oil was dissolved in toluene (10 mL)and 1.3 mL of NEt3 was added. The corresponding diol (1.8 mmol),((S,S)-2,3-butanediol in toluene (10 mL), (4S,5S)-4,5-di(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane and (R)-1,1?-bi-2-naphthol in THF (10 mL)) was added dropwise at 0 C. After 4 hof stirring, the white precipitate of triethylamine hydrochloridewas filtered off. The solvent was removed in vacuum and ayellowish oil was obtained and used without purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform; at 50℃; for 0.5h;Inert atmosphere; | General procedure: A 0.5-dram vial equipped with a magnetic stirring bar wascharged with stock solutions of 2-formylphenylboronicacid (0.10 M, 200 μL, 0.02 mmol), pinacol (0.10 M, 200 μL,0.02mmol) and 5c (0.25M, 80 μL, 0.02mmol). The solventswere removed in vacuo. CHCl3 (50 μL) was added undera positive pressure of argon. The reaction was stirred at 50C for 30 min. The volatiles were then removed under highvacuum. [Pd(allyl)Cl]2 (0.13 M in CHCl3, 40 μL, 5.0 μmol)was added under a positive pressure of argon and thereaction stirred at 23C for 15 min. Allyl acetate rac-7(0.01 M in CHCl3, 10 μL, 0.10 mmol), bis(trimethylsilyl)acetamide (49 μL, 0.20 mmol), diethyl malonate (30 μL,0.20 mmol) and potassium acetate (0.50 mg, 5.0 μmol)were added sequentially. The reaction was stirred at 23Cfor 24 hours. The crude reaction mixture was then filteredthrough a short plug of Celite and rinsed three times withCH2Cl2. An aliquot of the reaction mixture (5.0 μL) wasused for conversion and ee analyses using HPLC. HPLCconditions: Chiralpak IA column, 2.0% isopropanol/hexanes,0.5 mL/min, 254 nm, tr: 22.9 and 29.2min. |
A436587[ 18531-99-2 ]
(S)-[1,1'-Binaphthalene]-2,2'-diol
Reason: Optical isomers