Boron trifluoride etherate → 1-(4-Ethynylphenyl)-4-propyl-2,6,7-trioxabicyclo(2.2.2)octane
Reaction equation
[CH2:1]([C:4]1([CH2:8][OH:9])[CH2:7][O:6][CH2:5]1)[CH2:2][CH3:3].[Br:10][CH:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)[CH2:12][Br:13].B(F)(F)F.CCOCC>>[CH2:1]([C:4]12[CH2:8][O:9][C:18]([C:17]3[CH:21]=[CH:22][C:14]([C:11]#[CH:12])=[CH:15][CH:16]=3)([O:6][CH2:5]1)[O:19][CH2:7]2)[CH2:2][CH3:3].[CH2:1]([C:4]12[CH2:8][O:9][C:18]([C:17]3[CH:21]=[CH:22][C:14]([CH:11]([Br:10])[CH2:12][Br:13])=[CH:15][CH:16]=3)([O:6][CH2:5]1)[O:19][CH2:7]2)[CH2:2][CH3:3]Participants
Procedure
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).
Sources & evidence
- ORD record
- ord-f073304eece544b496edf521a5b64be1
- Source dataset
- uspto-grants-1988_09
- Patent number
- US04772624
Reaction notes
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