(+-)-3-Quinuclidinol → t-Butyl 2-(1-hydroxy-5-phenylpentyl)acrylate

HRID 1107173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107173
[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])(=[O:4])[CH:2]=[CH2:3].[C:10]1([CH2:16][CH2:17][CH2:18][CH2:19][CH:20]=[O:21])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N12CCC(CC1)C(O)C2>CCOCC>[OH:21][CH:20]([C:2](=[CH2:3])[C:1]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:19][CH2:18][CH2:17][CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

5

Edukt 3

HCID 15381(+-)-3-QuinuclidinolHCID 15458tert-Butyl acrylateHCID 561886Benzenepentanal

Produkt 1

HCID 18790144t-Butyl 2-(1-hydroxy-5-phenylpentyl)acrylateAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

t-Butyl acrylate (6.7 g, 46 mmol), 5-phenyl pentanal (3.7 g, 23 mmol) and 3-quinuclidinol (0.38 g, 3 mmol) are combined and stirred under N2. After 24 hours stirring is halted and the resulting solution is allowed to sit at ambient temperature for 16 days. TLC analysis (30% ether in petroleum ether) showed that the reaction is nearly complete. The product is purified by column chromatography (silica, 20% ether in petroleum ether) to yield t-butyl 2-(1-hydroxy-5-phenylpentyl)acrylate (6 g, 45%): 1H NMR (300 MHz, CDCl3) δ 7.29-7.24 (m, 2H), 7.18-7.14 (m, 3H), 6.10 (d, J=1.1 Hz, 1H), 5.67 (s, 1H), 4.33 (q, J=6.7 Hz, 1H), 2.74 (d, J=6.7 Hz, 1H), 2.61 (t, J=7.6 Hz, 2H), 1.70-1.53 (m, 4H), 1.50 (s, 9H), 1.50-1.32 (m, 2H); 13C NMR (75.5 MHz, CDCl3) δ 165.93, 143.91, 142.51, 128.32, 128.20, 125.57, 123.82, 81.35, 71.79, 36.17, 35.82, 31.26, 28.04, 25.54; MS (EI) m/e 291 (M+H)+.

Aufarbeitung

  1. stirringAfter 24 hours stirring
  2. customThe product is purified by column chromatography (silica, 20% ether in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-5b01093fe4fc42a4ae7354113f4de08d
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057369

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