p-Toluenesulfonic acid → 2-Methyl-3-butyn-2-yl 2-tetrahydropyranyl ether

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Reaction Steps

3-Methyl-1-butyn-3-ol (25 ml, 21.7 g), dihydropyran (50 ml) and p-toluenesulphonic acid (5 mg) were mixed together at 0° C. for 1 hr, and then stirred at room temperature for a further 40 hr. The mixture was concentrated and the reside added to 5% aqueous NaHCO3 and extracted with benzene. The organic solution was dried to give after distillation 37.3 g (86%) of the title ether. b.p. 47° C./0.8 mm Hg (lit. 30°-33° C./ 0.5 mm50 ; 57° C./3.5mm170); 1Hnmr δ 5.6 (m, THP C-2'H), 2.45 (s. C-1H), 1.51 (s, CH3), 1.48 (s, CH3); IR (thin film) 3350 s), 2950 (s), 2900 (sh), 112S (s), 1070 (s), 1030 (s), cm-1.

Provenance & Evidence