4-[2-(4-Butylphenyl)ethynyl]benzaldehyde → 6-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]-2,2-dimethyl-4H-1,3-benzodioxin-4-one
Reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C(O)(=O)C.[NH2:25][CH2:26][C:27]1[CH:39]=[CH:38][C:30]2[O:31][C:32]([CH3:37])([CH3:36])[O:33][C:34](=[O:35])[C:29]=2[CH:28]=1>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][NH:25][CH2:26][C:27]3[CH:39]=[CH:38][C:30]4[O:31][C:32]([CH3:37])([CH3:36])[O:33][C:34](=[O:35])[C:29]=4[CH:28]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
The titled compound was prepared following the procedure A using 4-[(4-butylphenyl)ethynyl]benzaldehyde and 6-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetate as a yellow oil (83%). 1H NMR (CDCl3, 300 MHz) δ 7.91 (s, 1H), 7.55 (m, 1H), 7.47 (d, J=7.9 Hz, 2H), 7.42 (d, J=7.9 Hz, 2H), 7.30 (d, J=8.3 Hz, 2H), 7.14 (m, 2H), 6.92 (d, J=8.3 Hz, 1H), 3.80 (s, 2H), 3.77 (s, 2H), 2.61 (m, 2H), 1.72 (s, 6H), 1.65-1.54 (m, 2H), 1.43-1.10 (m, 2H), 0.92 (m, 3H). M+ (ESI): 454.4. HPLC, Rt: 4.23 min (Purity: 100%).
Sources & evidence
- ORD record
- ord-16c41c633a2f4acdb7c74f360c01dff3
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07589232B2
Reaction notes
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