Sodium Hydroxide → HCID 86678080, compound

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1([CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[C:23]2[CH:22]=[C:21]([C:24]#[C:25]C(C)(O)C)[CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][C:14]([C:30]#[C:31]C(C)(O)C)=[CH:15][CH:16]=2.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(O)C>[C:30]([C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[C:23](=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=3)[C:11]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])([CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH3:45])[C:12]=2[CH:13]=1)#[CH:31]

Participants

Procedure

To a solution of 4,4′-[9,9-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene-2,7-diyl]bis(2-methyl-3-butyn-2-ol) (0.363 g, 0.58 mmol) in 9 mL of toluene and 2 mL of i-PrOH, was added solid NaOH (0.15 g, 3.75 mmol). The mixture was heated under reflux for 1.5 h. After cooling, NaOH was filtered off and the solvents were evaporated and the residue was purified by column chromatography on silica gel (CH2Cl2/AcOEt 60:40) to yield 0.171 g (58%) of 2,7-diethynyl-9,9-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene, mp 68° C.; 1H NMR (CDCl3) δ 2.37 (t, 4H, J=7.8 Hz), 2.74 (t, 4H, J=7.2 Hz), 3.17 (s, 2H), 3.20 (m, 4H), 3.35 (s, 6H), 3.39 (m, 4H), 3.54-3.47 (m, 8H), 7.50 (dd, 2H, J=7.8 Hz, J=1.3 Hz), 7.55 (d, 2H, J=1.3 Hz). 7.63 (d, 2H, J=7.8 Hz); 13C NMR (CDCl3) δ 39.5, 51.3, 59.1, 65.9, 66.8, 70.0, 70.4, 71.8, 77.9, 84.1, 120.1, 121.2, 127.0, 131.7, 140.2, 149.3. Anal. Calcd for C31H38O6 (506.63): C, 73.49; H, 7.56. Found: C, 73.59; H, 7.64.