Dimethylformamide → 2-Acetoxy-1-(naphth-1-yl)-1-propanone

HRID 33572Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33572
Br[CH:2]([CH3:15])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[C:16]([O-:19])(=[O:18])[CH3:17].[Na+].CN(C)C=[O:24]>>[C:5]1([CH:3]([O:4][C:16](=[O:18])[CH3:17])[C:2](=[O:24])[CH3:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.[CH3:15][CH:2]([O:19][C:16](=[O:18])[CH3:17])[C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Komponenten

5

Edukt 3

HCID 6228Dimethylformamide2×HCID 2311612-Bromo-1'-propionaphthoneHCID 517045Sodium Acetate

Produkt 2

HCID 51033133Acetic acid 1-naphthalen-1-yl-2-oxo-propyl esterHCID 597968292-Acetoxy-1-(naphth-1-yl)-1-propanoneAusbeute 49 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2-bromo-1-naphthalen-1-yl-propan-1-one (20 g), sodium acetate (7.8 g) and N,N-dimethylformamide (300 mL) was heated at 80° C. for 18 hours. After cooling to room temperature the N,N-dimethylformamide was removed under reduced pressure and the resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL). The organic phase was washed with water (300 mL), brine (300 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to afford acetic acid 1-naphthalen-1-yl-2-oxo-propyl ester and acetic acid 1-methyl-2-naphthalen-1-yl-2-oxo-ethyl ester (2:1 mixture) (9.0 g, 49%) as a brown oil, 1H NMR (CDCl3): 1.45 (3H, d, J=7.0 Hz), 2.05 (3H, s), 2.15 (3H, s), 2.2 (3H, s), 5.95 (1H, q, J=7.0 Hz), 6.65 (1H, s), 7.45-7.60 (7H, m), 7.85-7.90 (4H, m), 8.0 (1H, d, J=8.1 Hz), 8.1 (1H, d, J=8.3 Hz), 8.35 (1H, d, J=8.6 Hz).

Aufarbeitung

  1. customwas removed under reduced pressure
  2. customthe resulting residue was partitioned between dichloromethane (300 mL) and water (300 mL)
  3. washThe organic phase was washed with water (300 mL), brine (300 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-00208282f9144c10a73a4b4b26773f68
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429607B2

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