(E)-3-(m-Tolyl)acrylaldehyde → HCID 178424867, Verbindung

HRID 1404658Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1404658
[CH:1](=[C:8]1/[N:9]=[C:10]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[NH:11][C:12]/1=[O:13])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([CH3:32])[CH:27]=[CH:26][CH:25]=[C:24](/[CH:28]=[CH:29]/[CH:30]=[O:31])[CH:23]=1>>[F:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[C:10]1[NH:11][C:12]2[O:13][C:30](=[O:31])[CH:29]([CH2:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([CH3:32])[CH:23]=3)[CH:1]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[N:9]=1

Komponenten

3

Edukt 2

HCID 11788369(E)-3-(m-Tolyl)acrylaldehydeHCID 136341358(Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one

Produkt 1

HCID 178424867HCID 178424867, VerbindungAusbeute 61 %

Versuchsvorschrift

Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(m-tolyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 8 as an off-white solid (78 mg, 61%). Analytical data for 8: 1H NMR (500 MHz, CDCl3) δ 9.39 (d, J=7.3 Hz, 1H), 7.88 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.37-7.29 (m, 3H), 7.20-7.12 (m, 3H), 7.11-7.01 (m, 2H), 6.97 (ddd, J=6.2, 4.9, 1.9 Hz, 3H), 4.18 (d, J=6.9 Hz, 1H), 3.62 (ddd, J=9.7, 6.9, 4.8 Hz, 1H), 3.27 (dd, J=15.3, 4.8 Hz, 1H), 2.53 (dd, J=15.3, 9.8 Hz, 1H), 2.04 (s, 3H); 13C NMR (CDCl3, 126 MHz) δ 169.1, 159.1 (d, JCF=243.5 Hz), 155.4 (dd, JCF=241.0, 2.4 Hz), 148.8, 137.2, 136.7, 136.4, 135.9, 130.7, 129.3, 128.7, 128.3, 127.9, 126.7, 126.0, 118.4 (dd, JCF=12.8, 8.9 Hz), 117.1 (dd, JCF=25.8, 8.6 Hz), 116.6 (dd, JCF=24.8, 9.5 Hz), 114.5 (dd, JCF=26.8, 3.8 Hz), 110.9 (d, JCF=3.8 Hz), 45.6, 38.5, 29.5, 19.4; IR (film) cm−1 11773, 1636, 1618, 1529, 1481, 1463, 1452, 1411, 1240, 1171, 1122, 1100, 1078, 766, 747, 700; LRMS (ESI): Mass calcd for [M+H]+ C26H21F2N2O2: 431.2. found 431.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 4% IPA/2% MeOH/hexanes; 0.7 mL/min, 280 nm), Rt1 (minor)=39.1, Rt2 (major)=69.4 min; er=97:3.

Aufarbeitung

  1. customPrepared
  2. customThe unpurified residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4ab7ba71f3dc40e784f0bcc1e5f38588
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912341B2

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