Tetrahydrofuran → Tributyl(iodomethyl)stannane

Temperature

0 °C

To a mixture of triphenylphosphine (70 g, 0.27 mol) and tetrahydrofuran (500 mL) was added dropwise a mixture of N-iodosuccinimide (60 g, 0.27 mol) and tetrahydrofuran (500 mL) at 0° C., and then the reaction mixture was stirred for 30 minutes at 0° C. To this mixture was added dropwise tributylstannyl-methanol (71 g, 0.22 mol) described in Manufacturing Example 197-2-1 at 0° C., and then the reaction mixture was stirred for 20 minutes at 0° C. The reaction mixture was stirred overnight at room temperature. Diethyl ether and water were added to the reaction mixture, and the organic layer was separated. The organic layer was washed first with a saturated sodium thiosulfate aqueous solution and then with saturated aqueous sodium chloride. The organic layer was separated, and was concentrated under a reduced pressure. Heptane (400 mL) was added to the residue and filtered. The solvent in the filtrate was evaporated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane) to obtain the title compound (90 g, 94%).

1. additionwas added dropwise
2. customdescribed in Manufacturing Example 197-2-1 at 0° C.
3. stirringthe reaction mixture was stirred for 20 minutes at 0° C
4. stirringThe reaction mixture was stirred overnight at room temperature
5. customthe organic layer was separated
6. washThe organic layer was washed first with a saturated sodium thiosulfate aqueous solution
7. customThe organic layer was separated
8. concentrationwas concentrated under a reduced pressure
9. additionHeptane (400 mL) was added to the residue
10. filtrationfiltered
11. customThe solvent in the filtrate was evaporated under a reduced pressure
12. customthe residue was purified by silica gel column chromatography (heptane)

ORD record

ord-1068f42253e44096b40c2f18d050c6fe

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2