Ethyl 4-aminocinnamate → ethyl (2E)-3-{4-[(4-dec-1-ynylbenzyl)amino)phenyl}acrylate

HRID 733536Notes

Reaction equation

HRID 733536 reaction equation
[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[NH2:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:22][CH:21]=1>>[C:1]([C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:19][C:20]2[CH:21]=[CH:22][C:23](/[CH:26]=[CH:27]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:24][CH:25]=2)=[CH:13][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

3

Reactant 2

HCID 736317Ethyl 4-aminocinnamateHCID 578413204-Dec-1-ynylbenzaldehyde

Product 1

HCID 11200896ethyl (2E)-3-{4-[(4-dec-1-ynylbenzyl)amino)phenyl}acrylate

Procedure

The title compound was prepared following the procedure A using 4-dec-1-ynyl-benzaldehyde and ethyl (2E)-3-(4-aminophenyl)acrylate. (purification by flash chromatography on SiO2, EtOAc/c-Hex 1/7 to 1/6 in about 30 min.) as a yellow solid (61%). 1H NMR (CDCl3) δ: 7.59 (d, J=15.8 Hz, 1H), 7.36 (m, 4H), 7.26 (m, 2H), 6.57 (d, J=8.7 Hz, 2H), 6.21 (d, J=15.8 Hz, 1H), 4.35 (s, 2H), 4.23 (dd, J1=7.2 Hz, J2=14.3 Hz, 2H), 2.39 (t, J=7.2 Hz, 2H), 1.66-1.52 (m, 2H), 1.50-1.39 (m, 2H), 1.38-1.24 (m, 11H), 0.87 (m, 3H). M+ (ESI): 418.1; M− (ESI): 416.2. HPLC, Rt: 6.1 min (purity: 98.7%).

Workup

  1. custom(purification by flash chromatography on SiO2, EtOAc/c-Hex 1/7 to 1/6 in about 30 min.) as a yellow solid (61%)

Sources & evidence

ORD record
ord-8250e245c50e490eb6341f5cbb402870
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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