Triethylamine butyrolactone with

Elimination of hydrogen bromide from a-bromo-y-butyrolactone with triethylamine, 46,22 Epichlorohydrin, 46, 24 Ether, /-butyl phenyl, id, 89 /j-Ethoxyphenyl isothiocyanate, 46, 21 Ethyl acetoacetate, 46, 82 Ethyl benzoyloxy cyanoacetates, 46, 38 Ethyl y-BROMOBUTYRATE, 46, 42 Ethyl 2-biomocyclopentane acetate, 46, 44... 

Triethylamine, 46, 18 dehydrobromination of oi-bromo-y-butyrolactone with, 45, 23 Triethyl phosphonoacetate, reaction of sodium derivative with cyclohexanone to yield ethyl cyclo-hexylideneacetate, 46, 45 Trifluoroacetic anhydride, 45, 98 Teiphenylalctminum, 46,107... 

Tridecanedione, 47, 95 Triethylamine, 46,18 dehydrobromination of a-bromo-y-butyrolactone, 46, 23 dehydrobromination of o.a -dibromo-dibenzyl ketone, 47, 62 dehydrochlorination of cyclohexane-carbonyl chloride, 47, 34 in synthesis of nicotinic anhydride with phosgene, 47, 90 Triethylenetetramine, see Hexamethylenetetramine... 

B. A -Butenolide. In a 500-ml. three-necked flask fitted with a mechanical stirrer, a reflux condenser, and a 250-ml. dropping funnel containing a solution of 61 g. (84.5 ml., 0.6 mole) of triethylamine in 70 ml. of dry diethyl ether, a solution of 83 g. (0.5 mole) of a-bromo-Y-butyrolactone and 200 ml. of dry diethyl ether is heated to reflux, with stirring. The amine solution is added, slowly, during 5 hours and the stirring under reflux continued for an additional 24 hours. The brown precipitate (40 g.) is removed by filtration. Most of the solvent is removed from the filtrate by evaporation, and the additional precipitate (8 g.) is removed. This precipitate is predominantly triethylamine hydrobromide. The liquid residue is distilled under reduced pressure and the -butenolide is collected at 107-109° (24 mm.) ... 

A solution of triethylamine (39 ml 280.1 mmol 5 eq) in chloroform (100 ml) was added dropwise to a cooled (10°C) solution of aluminum chloride (22.4 g 168.1 mmol 3 eq) in chloroform (75 ml), the mixture was allowed to warm at room temperature. Ditetradecylamine chlorhydrate (7) (25 g 56 mmol, 1 eq) and butyrolactone (5.2 ml 67.2 mmol, 1.2 eq) in chloroform (350 ml) were then slowly added to the stirred mixture. After 2 h, the reaction medium was diluted with water (200 ml) and stirred for an additional 30 min. It was filtered over Celite, washing with chloroform. The organic phase was decanted and washed with NaClsat (3 X 150 ml), then dried over magnesium sulfate, filtrated and concentrated. Column chromatography on silica eluted with cyclo-hexane/ethyl acetate (1/1) gave 21.2 g (76%) of a white powder. 

Price and Judge effected dehydrobromination of a-bromo-y-butyrolactone (2) to y-crotonolactone (3) by reaction with triethylamine in ether. 

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