Triphenylphosphine → HCID 54063657, Verbindung

HRID 843140

Reaktionsgleichung

Reaktionsgleichung von HRID 843140
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[CH2:14]3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:26][OH:27].[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39](O)=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[CH2:28]([O:30][C:31]([C:33]1[O:34][C:35]2[CH:41]=[CH:40][C:39]([O:27][CH2:26][C:3]3[O:4][C:5]4[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH:13]5[CH2:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]6[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=6)[CH2:14]5)[C:6]=4[C:2]=3[CH3:1])=[CH:38][C:36]=2[CH:37]=1)=[O:32])[CH3:29]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22228632Ethyl 5-hydroxybenzofuran-2-carboxylateHCID 54356540[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol

Produkt 1

HCID 54063657HCID 54063657, VerbindungAusbeute 29,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[3-Methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-yl]-methanol (107 mg), 5-hydroxybenzofuran-2-carboxylic acid ethyl ester (60 mg), triphenylphosphine (100 mg) and azodicarboxylic acid diethyl ester (70 μl) were dissolved in THF (7 ml). The solution was stirred overnight at room temperature. A white precipitate separated out. The precipitate was filtered out and the filtrate was evaporated to dryness. The residue was separated by silica gel column chromatography developed by dichloromethane-methanol to give 5-[3-methyl-4-(1-pyridin-3-ylmethyl-piperidin-3-ylmethoxy)-benzofuran-2-ylmethoxy]-benzofuran-2-carboxylic acid ethyl ester (48 mg) as a colorless oil. FAB-MS: m/z 555 (MH+); 1H-NMR (CDCl3): δ 1.25-2.23 (7H, m), 1.43 (3H, t, J=7 Hz), 2.24 (3H, s), 2.78 (1H, m), 2.95 (1H, m), 3.47 (1H, d, J=13 Hz), 3.57 (1H, d, J=13 Hz), 3.89 (2H, m), 4.44 (2H, q, J=7 Hz), 5.10 (2H, s), 6.55 (1H, d, J=8 Hz), 7.04 (1H, d, J=8 Hz), 7.14 (1H, dd, J1=9 Hz, J2=2 Hz), 7.23 (3H, m), 7.47 (1H, m), 7.48 (1H, s), 7.66 (1H, br d, J=7 Hz), 8.48 (1H, br d, J=5 Hz), 8.53 (1H, br s).

Aufarbeitung

  1. customA white precipitate separated out
  2. filtrationThe precipitate was filtered out
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was separated by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f785f2041a364ae988fe6080d199f080
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06376491B1

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