HCID 59560812, compound → 1,2-Bis-dodecyloxy-4-ethynyl-benzene
Reaction equation
Br[C:2](Br)=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[C:6]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:5]=1.[Li]CCCC>C1COCC1>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]#[CH:2])=[CH:5][C:6]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
4-(2,2-Dibromo-vinyl)-1,2-bis-dodecyloxy-benzene (JYC-II-003-A) (9.0 g, 14.3 mmol) in 150 mL of dry THF was cooled down to −78° C. under Ar atmosphere. nBuLi (11.4 mL of 2.5 M solution in hexanes, 28.5 mmol) was added dropwise to the mixture and the resulting mixture was stirred at −78° C. for 1 h. The reaction mixture was allowed to warm up to room temperature and stirred at room temperature for additional 2 h. The reaction was quenched with a saturated NH4Cl aqueous solution and extracted with diethyl ether. The organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure. (The reaction did not go to completion and the product has very similar Rf value to that of the starting material.) The crude mixture was re-dissolved in dry THF and nBuLi (11.4 mL of 2.5 M solution in hexanes, 28.5 mmol) was added dropwise to the mixture. The mixture was stirred at room temperature for 2 h. The workup procedure was repeated. The product was further purified by column chromatography (silica gel, hexanes, then hexanes:dichloromethane=50:1 (v/v)) to give a white solid (4.38 g, 65.2%). 1H NMR (300 MHz, CDCl3, δ): 7.04 (dd, J=8.2 Hz, J=1.9 Hz, 1H), 6.97 (d, J=1.9 Hz, 1H), 6.77 (d, J=8.2 Hz, 1H), 3.97 (t, J=6.6 Hz, 2H), 3.95 (t, J=6.6 Hz, 2H), 2.96 (s, 1H), 1.74-1.84 (m, 4H), 1.20-1.50 (m, 36H), 0.87 (t, J=6.6 Hz, 6H). 13C{1H} NMR (75 MHz, CDCl3, δ): 149.87, 148.45, 125.36, 116.91, 113.93, 112.91, 83.92, 75.39, 69.18, 69.05, 32.00, 29.78, 29.73, 29.70, 29.48, 29.45, 29.22, 26.08, 22.78, 14.22. HRMS-EI (m/z): [M]+ calcd for C32H54O2, 470.4124; found, 470.4113. Anal. Calcd for C32H54O2,: C, 81.64; H, 11.56. Found: C, 81.36; H, 11.70.