1-Bromooctane → 2-[(Undec-2-yn-1-yl)oxy]oxane

Temperature

-78 °C

A solution of tetrahydro-2-(2-propynyloxy)-2H-pyran (47) (2.8 g, 20 mmol) in THF (30 mL) was cooled to -78° C. and n-BuLi (2.5 M, 8 mL) was added over 15 minutes. The mixture was stirred for 30 minutes at which time octyl bromide (4.24 g, 2.2 mmol, 1.1 equiv) in THF (10 mL) was added. The reaction mixture was then stirred at -78° C. for 1 hour, allowed to warm to 0° C. and stirred for an additional 30 minutes. The reaction mixture was quenched with NH4Cl (10 mL) and poured into ether (150 mL) and water (150 mL). The organic layer was separated, dried (MgSO4) and concentrated by rotary evaporation to yield a yellow oil used in the next step without purification. ##STR21##

1. additionwas added
2. temperatureto warm to 0° C.
3. stirringstirred for an additional 30 minutes
4. customThe reaction mixture was quenched with NH4Cl (10 mL)
5. additionpoured into ether (150 mL) and water (150 mL)
6. customThe organic layer was separated
7. dry with materialdried (MgSO4)
8. concentrationconcentrated by rotary evaporation
9. customto yield a yellow oil
10. customused in the next step without purification

ORD record

ord-7bd3e7c4578e44e18ef7c57620ee33e0

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238832