Ammonia → HCID 21432391, compound

Participants

Reaction Conditions

Reaction Steps

A solution of lithium amide (prepared from 3.5 g-atoms of lithium in 500 ml liquid NH2) was stirred at -30° C. while 2-methyl-2-(3-butynyl)-1,3-dioxolane (70.0 g, 0.5 mol) was added thereto dropwise over a 45 minute period. The solution was allowed to stir at -30° C. for 1 hour and subsequently cooled to -60° C.; 1-chloro-3-iodo-propane (103 g, 0.5 mol) then was added dropwise over a 30 minute period. After the addition was completed, the reaction was stirred at -30° C. for 4 hours. Solid NH4Cl (25 g, 0.47 mol) was added and the ammonia allowed to evaporate overnight. Water (200 ml) and ether (300 ml) were added to the solid residue and stirred for 15 minutes. The solution was filtered through infusorial earth (CELITE®) and the layers separated. The aqueous layer was further extracted with ether (2 × 200 ml) and the combined organic layers washed with water, brine, and dried over anhydrous MgSO4. Evaporation of the solvent gave 97 g of 2-methyl-2-(7-chloro-3-heptynyl)-1,3-dioxolane as an orange oil, bp 87°-88° C/ 0.15 mm. Yield: 65 g, 60%. NMR (CDCl3): 1.28(s, 3H); 1.67-2.52(m, 8H); 3.62(s, 2H); and 3.9(s, 4H).

Provenance & Evidence