Boron trifluoride etherate → 1-(4-Ethynylphenyl)-4-propyl-2,6,7-trioxabicyclo(2.2.2)octane

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Reaction Steps

The compound 4-n-propyl-1-(4-ethynylphenyl)-2,6,7-trioxabicyclo[2.2.2]octane was synthesized utilizing the method set forth in Procedure 2. Reaction of the 3-n-propyl-3-hydroxymethyloxetane with 4-(1,2-dibromoethyl)benzoyl chloride led to the production of the corresponding oxetane ester which was characterized by NMR (300 MHz, CDCl3): δ 0.95 (3H, t, CH3), 1.35 (2H, m, CH3CH2), 1.75 (2H, m, CH3CH2CH2), 3.95-4.1 (2H, m, CH2Br), 4.45 (2H, s, CH2O), 4.5-4.6 (4H, d of d, CH2OCH2), 5.1 (1H, d of d, ArCHBr), 7.5 (2H, d, aromatic), 8.05 (2H, d, aromatic). The oxetane ester was reacted with boron trifluoride etherate as described in Procedure 2 to provide 4-n-propyl-1-(4-(1,2-dibromoethyl)phenyl)-2,6,7-trioxabicyclo[2.2.2]octane. This compound was characterized by NMR (300 MHz, CDCl3): δ 0.9 (3H, t, CH3), 1.15-1.35 (4H, m, CH2CH2), 3.9-4.1 (2H, m, CH2Br), 4.1 (6H, s, (CH2O)3), 5.1 (1H, d of d, ArCHBr), 7.35 (2H, d, aromatic), 7.6 (2H, d, aromatic).

Provenance & Evidence