反应详情

温度

6 °C

A solution of 2-bromothioanisole (1.05 g) in 20 mL of anhydrous tetrahydrofuran was cooled to -78° C. and treated with 2 mL of 2.5M hexane solution of n-butyl lithium. After the addition was complete the reaction mixture was stirred for 30 minutes and then treated with a solution of N-benzyloxycarbonyl-4-oxopiperidine (1.17 g) in 1 mL of tetrahydrofuran. After stirring at -78° C. for 30 minutes the reaction mixture was allowed to warm to 6° C. and treated with 10 mL of water. Upon extracting with ethyl acetate, drying and evaporation, the organic layer afforded the crude product. This material was purified by chromatography; elution with 6:4 hexane:ethyl acetate afforded the named material (0.27 g); MS: 358; NMR: 1.9-2.1 (b, 4), 2.5 (s, 3), 3.4 (b, 2), 4.1b (b, 2), 5.1 (s, 2), 7.1-7.5 (m, 9).

1. additionAfter the addition
2. stirringAfter stirring at -78° C. for 30 minutes the reaction mixture
3. extractionUpon extracting with ethyl acetate
4. customdrying
5. customevaporation
6. customthe organic layer afforded the crude product
7. customThis material was purified by chromatography
8. washelution with 6:4 hexane