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CAS No. : | 10229-10-4 | MDL No. : | MFCD00002956 |
Formula : | C5H8O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 84.12 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Danger | Class: | 3 |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | 1987 |
Hazard Statements: | H225-H315-H319-H335 | 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 |
---|---|---|
96% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 3h; Ambient temperature; | |
95% | Stage #1: pent-3-yn-1-ol; N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran for 0.166667h; Inert atmosphere; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 25℃; for 12h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With toluene-4-sulfonic acid In toluene at 130℃; for 6h; Dean-Stark; | |
84% | With toluene-4-sulfonic acid In benzene for 7h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; sodium hydroxide | 6 6.) 6.) 3,4-Dimethoxy-1-[1-(pent-3-ynyloxyl)ethyl]benzene Into a flask, equipped with stirrer, 1.5 g (8.23 mmol) of α-methylveratryl alcohol and 1.4 g (16.46 mmol) of 3-pentyn-1-ol are placed and to the mixture 3.0 ml of the 50 w/v % calcium chloride-1 w/w % hydrochloric acid solution is added, at a fast rate. The mixture is stirred overnight at room temperature, then it is diluted with ether, and the mixture is neutralized with a few drops of 1 M sodium hydroxide solution. The two phases are separated, the aqueous phase is thoroughly extracted with ether. The united organic phase is washed with saturated sodium chloride solution, dried and evaporated. Yield: 1.9 g (93%). GC (CP 9000, CP-SIL-5CB, 60 m*0.53 mm, 5 ml/min N2, FID, 250° C.) tR=5.0 min, approx. 93.2%. IR (CDCl3, cm-1) υ: 2995, 2974, 2957, 2864, 2838, 1607, 1595, 1510, 1465, 1260, 1163, 1142, 1098, 1027. 1H-NMR (200 MHz, CDCl3) δ: 1.44 (3H, d, J=6.4 Hz, CH-CH3), 1.75 (3H, t, J=2.5 Hz, CH3-C≡), 2.37 (2H, m, CH2-C≡), 3.38 (2H, t, J=7.2 Hz), 3.87 and 3.89 (altogether 6H, each s, OCH3), 4.38 (2H, q, J=6.4 Hz, Ar-CHO), 6.83 (2H, d, aromatic), 6.90 (1H, s, aromatic). 13C-NMR(50 MHz, CDCl3) δ: 3.42 (CH3-C≡), 20.27 (OCH2-CH2), 24.07 (CH-CH3), 55.78 s 55.85 (OCH3), 67.04 (OCH2-CH2), 75.93 and 77.78 (Ar-CH-CH3, C≡C two signals overlapping), 108.92 (C-2), 110.83 (C-5), 118.52 (C-6), 136.34 (C-1), 148.33 (C-3), 149.13 (C-4). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: pent-3-yn-1-ol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 0.5h; Stage #2: With triethylamine In dichloromethane for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 18h; | A mixture of pent-3-yn-1-ol (60 g, 710 mmol), <strong>[5455-59-4]2-nitrobenzenesulfonamide</strong> (15 g, 74 mmol), and triphenylphosphine (97 g, 370 mmol) in tetrahydrofuran (THF) (300 ml_) was treated dropwise with DIAD (57.7 ml_, 297 mmol). After 18 h, the reaction mixture was concentrated in vacuo. The resulting oil was treated with a 1 :4 mixture of EtOAc:hexanes and the solids collected by filtration. The filtrate was concentrated in vacuo and purified by silica chromatography (0-50% DCM:hexanes). The residue was suspended in 1 :1 ethyl ether/hexanes and cooled to 0 C and the solids collected by vacuum filtration to afford the title compound (18 g, 51 mmol, 69% yield) as a white powder. H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.0 - 8.2 (m, 1 H), 7.6 - 7.8 (m, 3 H), 3.5 (t, J=7.33 Hz, 4 H), 2.4 (ddd, J=9.66, 4.99, 2.56 Hz, 4 H), 1.7 (t, J=2.56 Hz, 6 H). LCMS (ES+)(m/z): 335.3 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With copper(l) iodide; N<SUP>1</SUP>, N<SUP>2</SUP>-diphenethyloxalamide; sodium t-butanolate In 1,4-dioxane for 24h; Schlenk technique; Inert atmosphere; Molecular sieve; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Candida antarctica lipase B immobilized on a macroporous acrylic resin at 40℃; for 42h; Green chemistry; Enzymatic reaction; | General experiment for the optimised acetylation of alcohols, according to Scheme 2: General procedure: Lipozyme 435 (2% wt) was added to a solution of an alcohol (1 equiv) in EGDA (2 equiv).The reaction mixture was incubated in an orbital shaker (40 °C, 150 rpm) and the reaction progress wasmonitored by GC-FID (see Table 1). |