Hantzsch ester → 3-Hydroxy-2-(3-(2-((triisopropylsilyl)oxy)ethyl)benzyl)cyclopent-2-enone

HRID 41146

Reaktionsgleichung

Reaktionsgleichung von HRID 41146
[CH:1]([Si:4]([CH:19]([CH3:21])[CH3:20])([CH:16]([CH3:18])[CH3:17])[O:5][CH2:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)([CH3:3])[CH3:2].[CH2:22]1[C:27](=[O:28])[CH2:26][C:24](=[O:25])[CH2:23]1.N1CCC[C@H]1C(O)=O.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>ClCCl>[OH:25][C:24]1[CH2:23][CH2:22][C:27](=[O:28])[C:26]=1[CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([CH2:7][CH2:6][O:5][Si:4]([CH:19]([CH3:21])[CH3:20])([CH:1]([CH3:3])[CH3:2])[CH:16]([CH3:18])[CH3:17])[CH:9]=1

Komponenten

6

Edukt 4

HCID 70849Hantzsch esterHCID 774661,3-CyclopentanedioneHCID 145742L-ProlineHCID 547576553-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehyde

Produkt 1

HCID 547578633-Hydroxy-2-(3-(2-((triisopropylsilyl)oxy)ethyl)benzyl)cyclopent-2-enoneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 14 (0.920 g, 3.0 mmol), 1,3-cyclopentadione (0.098 g, 1.0 mmol), and L-proline (0.005 mg) in dichloromethane (5 mL), diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (0.253 g, 1.0 mmol) was added, and the resulting mixture was allowed to stir at rt for 12 h. The reaction mixture was directly purified by silica gel column chromatography using a gradient of ethyl acetate in hexanes as eluent, obtaining the title compound. Yield: 76%.

Aufarbeitung

  1. customThe reaction mixture was directly purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-aeec9718dc6944e796d68c0a7954f05e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530520B2

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