Tributyltin Chloride → 5-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan

Temperature

-78 °C

2-(4-Methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)furan (2.0 g, 10.2 mmol) was dissolved in THF (20 ml) and the solution was cooled to −78° C. n-BuLi (1.6 M solution in hexanes, 7.7 ml, 12.32 mmol) was added and the mixture stirred at −78° C. for 30 min, allowed to warm to 0° C. for 20 min. and then recooled to −78° C. The tributyltin chloride (3.5 ml, 4.68 g, 14.4 mmol) was added and stirring was continued at −78° C. for 15 min. The mixture was allowed to warm gradually to room temperature and stirring continued for three days. The reaction was quenched by the addition of water, and extracted with ethyl acetate. This solution was washed with water, dried (MgSO4), and concentrated in vacuo to give the title compound as a yellow oil (4.7 g, 9.7 mmol, 95%); δH [2H6]DMSO 6.52 (1H, d), 6.38 (1H, d), 3.96 (6H, s), 0.77-1.63 (30H, m).

1. additionwas added
2. temperatureto warm to 0° C. for 20 min.
3. customrecooled to −78° C
4. stirringstirring
5. waitwas continued at −78° C. for 15 min
6. temperatureto warm gradually to room temperature
7. stirringstirring
8. waitcontinued for three days
9. customThe reaction was quenched by the addition of water
10. extractionextracted with ethyl acetate
11. washThis solution was washed with water
12. dry with materialdried (MgSO4)
13. concentrationconcentrated in vacuo

ORD record

ord-8314f6e3cbbc4b19b3d198edef5fc497

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06828320B2