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

Participants

Reaction Conditions

Reaction Steps

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##

Provenance & Evidence