Y-Chlorobutyryl chloride

Aluminum chloride Fluorobenzene y-Chlorobutyryl chloride l-(o-Anisyl)piperazine... 

To a suspension of 341 parts of aluminum chloride in 1740 parts of carbon disulfide are added 96 parts of fluorobenzene with stirring and cooling. While the temperature is maintained at about 10°C, 141 parts of y-chlorobutyryl chloride are added. After the addition is completed, the cooling bath is removed and the stirring is continued for 2 hours. The reaction mixture is poured into ice water. The organic layer is separated, washed with water, dried over anhydrous sodium sulfate, and filtered. The filtrate is concentrated under reduced pressure, and the residue is distilled to yield y-chloro-p-fluoro-butyrophenone boiling at about 136°-142°C/6 mm. 

The diamide 93, prepared from anthranilamide and y-chlorobutyryl chloride, was cyclized in the presence of sodium methoxide by Land Vittory and Gatta. The reaction yielded a mixture of the linearly and angularly fused tricyclic compounds 95 and 94. The pyrrolo[l,2-a]quinazoline 94 was also prepared from the ester 96 by treatment with methanolic ammonia. ... 

Taylor and Shvo" obtained a good yield of the pyrrolo[ 1,2-a]quinazoline 94 from anthranilonitrile and y-chlorobutyryl chloride. Ring closure was effected with dry gaseous hydrogen chloride. 

Jacobi and co-workers ° described the total synthesis of racemic stemoamide, a member of the stemona alkaloids isolated in 1992 from Stemona tuberosa, and an enantioselective route to (-)-stemoamide. The starting alkyne oxazoles 200 and 203 were prepared from y-chlorobutyryl chloride 199 in five steps (Fig. 3.60). 

Chlorobutyryl chloride added with vigorous stirring during 50 min. to dry KF in sulfolane with spontaneous distillation of the product from the exothermic reaction at such a rate that the temp, in the take-off head is kept at 80-100° -> cycloprop anecar boxy lie acid fluoride. Y 70.4%. Also from the 4-bromo analog s. R. E. A. Dear and E. E. Gilbert, J. Org. Chem. 33, 1690 (1968). 

A 0.38 N soln. of Ag-tetrafluoroborate in methylene chloride-benzene added dropwise at —20 with agitation to a soln. of ( + )-Na-(y-chlorobutyryl)-L-tryptophan methyl ester in abs. methylene chloride, kept 1 hr. at —20 , agitated 1 hr. at 0°, after an additional 1.5 hrs. at room temp, excess Ag-tetrafluoroborate decomposed with triethylamine hydrochloride, the resulting crude imino-lactone dissolved in acetonitrile treated with methyl iodide, stored 41 hrs. at 30 , excess methyl iodide and 2/3 of the acetonitrile evaporated in vacuo at room temp., the residual soln. allowed to stand 2 hrs. at 20 with 2 N KHGO3-soln., and the product isolated as the hydrochloride (+)-Ngj-methyl-L-trypto-phan methyl ester hydrochloride. Y 84.5%. H. Peter et al., Helv. 46, 577 (1963). 

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