反应详情

To a mixture of 21.8 g (0.083 moles) of triphenyl phosphine stirred in 30 ml acetonitrile, 13.2 g (4.26 ml) bromine in 75 ml acetonitrile was added dropwise with stirring in an ice bath. After the addition was complete, the ice bath was removed and the mixture warmed to room temperature. Then a mixture of 12.1 g (0.075 mole) of 3-(3-cyanophenyl)-1-propanol (the product of step (b)) in 30 ml acetonitrile was added dropwise. The resulting mixture was allowed to warm to about 45°-50° C., was stirred overnight and then stripped. Benzene (50 ml) was added to the residue; the mixture was evaporated. Then, additional benzene (50 ml) was added. The mixture was stirred, and then filtered to remove the triphenyl phosphine. The filtrate was stripped to give an oil. The oil was chromatographed using a column containing 3.5 inches of 200 mesh silica gel (Merck) eluting with benzene, until TLC showed that no further product was eluted from the column. The eluates were pooled and stripped to give 17 g of an oil. The oil was distilled in a Kugelrohr apparatus, the fraction bpt. 102°-103° C. was collected to give 15.7 g of the above-identified product as an oil.

1. additionAfter the addition
2. customthe ice bath was removed
3. additionwas added dropwise
4. temperatureto warm to about 45°-50° C.
5. stirringwas stirred overnight
6. customthe mixture was evaporated
7. additionThen, additional benzene (50 ml) was added
8. stirringThe mixture was stirred
9. filtrationfiltered
10. customto remove the triphenyl phosphine
11. customto give an oil
12. customThe oil was chromatographed
13. additioncontaining 3.5 inches of 200 mesh silica gel (Merck)
14. washeluting with benzene, until TLC
15. washwas eluted from the column