[CH2:1]([O:6][CH2:7][C:8]#[CH:9])[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:10]([O:12]CC)C.C([Li])CCC.C=O>CCCCCC.O>[CH2:1]([O:6][CH2:7][C:8]#[C:9][CH2:10][OH:12])[CH2:2][CH2:3][CH2:4][CH3:5]
To a 500 mL 3 neck flask equipped with magnetic stirrer, addition funnel, and nitrogen inlet was charged 10 grams (g) of 3-(pentyloxy)prop-1-yne (0.72 mmol), and 140 mL of dry ethyl ether. The reaction mixture was cooled to −78° C. with stirring followed by the dropwise addition of 37.5 mls (60 mmole) of 1.6M n-Butyl lithium solution in hexane. The temperature was adjusted to 0° C. and 5.4 g (180 mmole) of solid paraformaldehyde was added. The mixture was then stirred at ambient temperature overnight. Ether and water was added to the mixture and the ether layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated under vacuum on a rotary evaporator. Isolated 9.44 g of a colorless liquid which was consistent with the desired structure upon analysis by 300 MHz 1H NMR.
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