Water → 4-Methoxybenzoic acid, 6-aminohexyl ester

HRID 1281430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281430
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]=[N+]=[N-])=[O:8])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[O:8])=[CH:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 865836674-Methoxybenzoic acid, 6-azidohexyl ester

Produkt 1

HCID 572173864-Methoxybenzoic acid, 6-aminohexyl esterAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 4-methoxybenzoic acid, 6-azidohexyl ester (1.119 g, 4.035 mmol), triphenylphosphine (1.164 g, 4.439 mmol), and water (0.08 ml) in THF was stirred under nitrogen at room temperature. After 144 h, the reaction mixture was diluted with EtOAc (50 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient) to give the desired product as a light yellow oil (0.0796 g, 78%); 1H NMR (400 MHz, DMSO-d6)δ 1.18-1.40 (m, 6H), 1.63-1.71 (m, 2H), 2.50 (t, J=6.4 Hz, 2H), 3.82 (s, 3H), 4.21 (t, J=6.6 Hz, 2H), 7.01-7.06 (m, 2H), 7.87-7.92 (m, 2H); IR (KBr) 3410 (broad), 2940, 1710, 1605, 1510, 1260 cm−; mass spectrum[(+)ESI], m/z 252 (M+H)+.

Aufarbeitung

  1. dry with materialdried over Na2SO4
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated in vac
  4. customdried
  5. customThe residue was purified by flash chromatography (2×)(alumina, chloroform to 10% MeOH/CHCl3 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-c0da81e78e48430c89bb7f07ff74ddfd
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06451827B2

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