CAS RN: 90965-06-3 | Product Number: D3546
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|Purity / Analysis Method||>97.0%(HPLC)|
|Molecular Formula / Molecular Weight||C__5H__9N__2O__4P = 192.11|
|Physical State (20 deg.C)||Liquid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Air Sensitive,Heat Sensitive|
|Reaxys Registry Number||4247670|
|PubChem Substance ID||87559944|
|Merck Index (14)||1177|
|Appearance||Light yellow to Brown clear liquid|
|Purity(HPLC)||min. 97.0 area%|
|Specific Gravity (20/20)||1.28|
To a methanol (10 mL) solution of undecanal (0.20 g, 1.2 mmol) was added potassium carbonate (0.32 g，2.4 mmol) and Ohira-Bestmann reagent (0.27 g, 1.4 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature, then diluted with diethyl ether and washed with saturated aqueous sodium bicarbonate, and dried by sodium sulfate. The organic layer was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane:toluene = 3:1 on silica gel) to give 1 as a colorless liquid (0.11 g, 56% yield).
The reaction mixtures were monitored by 1H NMR (CDCl3).
Analytical Data（1-Dodecyne (1)）
1H NMR (400 MHz, CDCl3); δ 2.18 (t, 2H, J = 7.1 Hz), 1.94 (s, 1H), 1.57-1.46 (m, 2H), 1.44-1.33 (m, 2H), 1.33-1.19 (m, 12H), 0.88 (t, 3H, J = 6.4 Hz).
13C NMR (101 MHz, CDCl3); δ 85.0, 68.2, 32.0, 29.7, 29.7, 29.5, 29.3, 28.9, 28.6, 22.8, 18.5, 14.3.
- Further Improvements of the Synthesis of Alkynes from Aldehydes
- Methanolysis of Dimethyl (1-Diazo-2-oxopropyl) Phosphonate: Generation of Dimethyl (Diazomethyl) Phosphonate and Reaction with Carbonyl Compounds
- K. Mohanan, A. R. Martin, L. Toupet, M. Smietana, J.-J. Vasseur, Angew. Chem. Int. Ed. 2010, 49, 3196.
- S. Ohira, Synth. Commun. 1989, 19, 561.
- S. Muller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521.
- H. D. Dickson, S. C. Smith, K. W. Hinkle, Tetrahedron Lett. 2004, 45, 5597.
- E. Quesada, R. J. K. Taylor, Tetrahedron Lett. 2005, 46, 6473.
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