1-Bromo-6-fluorohexane → 2-[(10-Fluorodec-3-YN-1-YL)oxy]oxane

Participants

Reaction Steps

Repetition of the procedure described in Example 3 using 0.7992 g (5.06 mmol) of 3-butyn-1-yl tetrahydropyranyl ether, 3.6 mL (5.06 mmol) of 1.39M n-butyl lithium in hexane and 1.117 g (6.07 mmol, 1.2 eq) of 6-fluoro-1-bromo-hexane followed by purification by flash chromatography affords 10-fluoro-3-decyn-1-yl tetrahydropyranyl ether (570 mg, 44%) as a clear colorless oil: Rf=0.58 hexane/ethyl acetate (7:3, v/v); IR (film) ν2850-2950 (alcane CH); and 1H-NMR (CDCl3) δ1.20-1.95 (m, 14H), 2.15 (m, 2H), 2.45 (m, 2H), 3.65 (m, 4H), 4.42 (dt, J=48 Hz, 6 Hz, 2H), 4.65 (br s, 1H).

Provenance & Evidence