Sulfuric Acid → Ethyl 1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxylate
Reaktionsgleichung
[C:1]1([C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8]([CH:10]([C:16](OCC)=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O>O>[OH:17][C:16]1[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:7]([CH2:24][CH2:25][CH3:26])([CH2:21][CH2:22][CH3:23])[C:8](=[O:9])[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
The product of Example 1E (4.51 g, 12.4 mmol) was treated with concentrated sulfuric acid (25 mL) and stirred at 25° C. for 3 hours. The mixture was then poured into a mixture of ice and water (500 mL) and stirred until all the ice melted. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with water and saturated sodium chloride solution, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with methyl t-butyl ether in hexane to afford the title compound (1.73 g, 44%). 1H NMR (300 MHz, CDCl3): δ 15.15 (d, J=13.24 Hz, 1 H), 8.18 (m, 1 H), 7.59 (m, 1 H), 7.40 (m, 2 H), 4.47 (m, 2 H), 2.25 (m, 2 H), 1.91 (m, 1H), 1.70 (m, 1 H), 1.47 (q, J=7.23 Hz, 3 H), 1.25 (m, 1 H), 0.93 (m, 2 H), 0.67 (m, 7 H).
Aufarbeitung
- extractionThe mixture was extracted with ethyl acetate (2×)
- washThe combined organic layers were washed with water and saturated sodium chloride solution
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel
- washeluting with methyl t-butyl ether in hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-45898439cd334ccbbc74c0848fa835ae
- Quelldatensatz
- uspto-grants-2009_05
- Patentnummer
- US07538105B2
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