Pyridine → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetate

HRID 494659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494659
[CH3:1][O:2][C:3]1[C:4]([CH2:18][OH:19])([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:20](OC(=O)C)(=[O:22])[CH3:21].N1C=CC=CC=1>O>[C:20]([O:19][CH2:18][C:4]1([CH2:13][CH2:14][CH:15]([CH3:16])[CH3:17])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:11][CH:12]=[C:3]1[O:2][CH3:1])(=[O:22])[CH3:21]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 68871071[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol

Produkt 1

HCID 68872462[2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methyl acetateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of Example 179A (0.18 g, 0.7 mmol), acetic anhydride (0.2 mL), and pyridin (1 mL) was stirred at room temperature for 18 h. The solution was diluted with water (3 mL) and extracted with ethyl acetate (2× 1 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (hexane to 5% ethyl acetate/hexane) afforded product as a colorless oil (0.17 g, 81%). 1H NMR (300 MHz, CDCl3) δ ppm 0.66 (m, 1H), 0.76 (dd, J=9.56, 6.62 Hz, 6H), 0.89 (m, 1H), 1.38 (m, 1H), 1.61 (m, 1H), 1.81 (s, 3H), 1.95 (m, 1H), 3.50 (s, 2H), 3.58 (s, 3H), 4.24 (d, J=10.66 Hz, 1H), 4.42 (d, J=10.66 Hz, 1H), 5.01 (t, J=3.49 Hz, 1H), 7.20 (m, 4H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2× 1 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-37d9b5aab7394de896e5a43d1f195122
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538105B2

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