DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Tuesday 1 December 2015

3-Methyl-1-hexen-5-yn-3-ol




   Reaction Scheme: <IMG src="/images/empty.gif"><IMG src="/images/empty.gif"><IMG src="/images/empty.gif">In situ propargyl Grignard addition to vinylic ketone<IMG src="/images/empty.gif"><IMG src="/images/empty.gif"><IMG src="/images/empty.gif">.



 

3-Methyl-1-hexen-5-yn-3-ol
b.p. 54-55°/25 mm, nD22 1.4576, d425 0.8930.

Ir (neat film)  3400(s, OH stretch), 3300(s, alkyn C-H stretch), 3040(m,=C-H stretch),2950(m), 2930(m), 2910(m), 2120(w), 1640(m, C=C stretch), 1450(m), 1410(s), 1370 (s, CH3), 1270(m), 1240(m), 1170(m), 1110(s), 995(m), 920(s), 870(m), 760(m), 750(m), and 650(v.s.) cm-1.

1H Nmr (60MHz, CDCl3) δ, singlet at 1.40 (3H, Methyl), a doublet at 2.45, (2H, aliphatics), a broad singlet at 3.35,1H, hydroxyl), a doublet of doublets centered at 5.10 and 5.30 (total 2H, terminal vinyl), and a doublet of doublets at   6.10(1H, internal vinyl).




1)    Alfred Viola and John H. MacMillan, "A Novel Steric Effect in the Thermolysis of Prop-2-ynyl Vinyl Carbinols" Chemical Communications, p 301, (1970). DOI: 10.1039/C29700000301

1)      F. Sondheimer, Y. Amiel, and Y. Gaoni, J. Amer. Chem. Soc., 84, 270-274, (1962).
DOI: 10.1021/ja00861a029
2)      A. Viola and J.H. MacMillan, J. Amer. Chem. Soc., 90, 6141, (1968).
DOI: 10.1021/ja01024a035
3)        Triple Bond Participation in the Oxy-Cope Rearrangement", John H. MacMillan, Ph.D. Thesis, Northeastern University, 1970, Dissertation Abstracts International, Order Number 72-13,297. http://dissexpress.umi.com/dxweb/results.html?QryTxt=&By=John+Harry+MacMillan&Title=&pubnum=7213297



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