Acetophenone → 1-(Naphthalen-2-yl)-3-phenylpropane-1,3-dione

HRID 1522322

Reaktionsgleichung

Reaktionsgleichung von HRID 1522322
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[C:20]([O:22]C)=O.[H-].[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[C:20]([CH2:2][C:1](=[O:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:22]

Komponenten

6

Edukt 4

HCID 7410AcetophenoneHCID 24758Sodium hydrideHCID 137605Methyl 2-naphthoateHCID 516892Sodium Bicarbonate

Produkt 1

HCID 186949701-(Naphthalen-2-yl)-3-phenylpropane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Acetophenone (500 mg, 4.12 mmol), methyl 2-naphthoate (1.03 g, 5.36 mmol) and THF (20 mL) were added sequentially to a 50 mL round bottom flask. After stirring the mixture for 10 min, a suspension containing NaH (167 mg, 6.61 mmol) in THF (10 mL) was added dropwise at room temperature under N2. The mixture was stirred for 20 h before saturated aqueous NaHCO3 (1 mL) was added to quench the reaction. THF was removed in vacuo before 1 M HCl (20 mL) was added. The aqueous phase was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with distilled water (2×10 mL) and brine (10 mL), and dried over Na2SO4 before concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (6:1) to give 2-naphthoyl benzoylmethane, thin, as a yellow solid: 700 mg (62%). 1H NMR (300 MHz, CDCl3) δ 16.98 (s, 1H, ArCOH), 8.62 (s, 1H, 1′-ArH), 8.08-7.87 (m, 6H, 3′, 4′, 5′, 2″, 6″-ArH), 7.62-7.49 (m, 5H, 6′,7′-ArH. 3″, 4″, 5″-ArH), 7.01 (s, 1H, COCHCO); MS (MALDI) m/z 275.13 (M+H+), calcd m/z 275.11.

Aufarbeitung

  1. additionwas added dropwise at room temperature under N2
  2. additionwas added
  3. customto quench
  4. customthe reaction
  5. customTHF was removed in vacuo before 1 M HCl (20 mL)
  6. additionwas added
  7. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
  8. washThe combined organic layers were washed with distilled water (2×10 mL) and brine (10 mL)
  9. dry with materialdried over Na2SO4
  10. concentrationbefore concentrated in vacuo
  11. customThe residue was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (6:1)

Quellen und Nachweise

ORD-Eintrag
ord-53c76c27b9d8463fb0647a3625303d99
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09074129B2

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