反应详情

TsCl (955 mg, 5.0 mmol) and pyridine (435 μL, 5.4 mmol) were added to a solution of 7-azidoheptanol (700 mg, 4.5 mmol) in CH2Cl2 (5 mL). The solution was stirred for 18 h at r.t. The solution was diluted with EtOAc (20 mL) and washed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer. The org. layer was concentrated and the residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl. The mixture was diluted with EtOAc (20 mL), washed with aqueous NaHCO3, dried (Na2SO4), and filtered. Concentration under reduced pressure yielded 7-azidoheptyltosylate (920 mg, 66%). The product was pure enough for further reactions.

1. washwashed with 5% aqueous KHSO4 solution, sat. aqueous NaHCO3 solution and pH 7 phosphate buffer
2. concentrationlayer was concentrated
3. additionthe residue was treated with water (10 mL) for 4 h to hydrolyse excess TsCl
4. additionThe mixture was diluted with EtOAc (20 mL)
5. washwashed with aqueous NaHCO3
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationConcentration under reduced pressure