1,1'-Carbonyldiimidazole → 7-Nitro-1-phenylundecan-6-one

HRID 929412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929412
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[N+:27]([CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])([O-:29])=[O:28].C1CCN2C(=NCCC2)CC1>>[N+:27]([CH:30]([CH2:31][CH2:32][CH2:33][CH3:34])[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([O-:29])=[O:28]

Komponenten

5

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 796956-Phenylhexanoic AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2206391-Nitropentane

Produkt 1

HCID 468485147-Nitro-1-phenylundecan-6-one

Versuchsvorschrift

6-Phenylhexanoic acid (0.100 g, 0.52 mmol) and CDI (0.169 g, 1.04 mmol) were added together and then reacted with nitropentane (0.091 g, 0.78 mmol) and DBU (0.198 g, 1.30 mmol) according to the general procedure. Purification by column chromatography gave 0.049 g (32%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 7.28 (m, 2H), 7.17 (m, 3H), 5.10 (dd, J=4.4, 10.0 Hz, 1H), 2.61 (m, 4H), 1.63 (m, 6H), 1.35 (m, 6H) 0.92 (t, J=6.8 Hz, 3H) ppm; 13C NMR (100 MHz, CDCl3) δ 199.5, 142.5, 128.6, 128.5, 126.0, 94.5, 39.5, 35.9, 31.3, 29.6, 28.7, 28.1, 23.3, 22.2, 13.9 ppm; IR νmax (cm−1) 3027, 2931, 2859, 1731, 1559, 1454, 1363, 1030, 748, 700; HRMS (FAB) calcd for C17H25NO3 (MNa+) 314.1727, found 314.1722.

Aufarbeitung

  1. customPurification by column chromatography
  2. customgave 0.049 g (32%) as a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-376bb607a3d74aca9667b45df8d90865
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09295257B2

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