Reaktion #1564464

Reaktionsgleichung

Sodium hydride

6-hydroxycoumarin

1-Bromo-3,7-dimethyloctane

→

desired product

6-((3,7-dimethyloctyl)oxy)-2H-chromen-2-one

Lösungsmittel

N,N-dimethylformamide

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven dried 50 mL round bottom flask
2. 2
   Sonstigewas prepared with a magnetic stirring bar
3. 3
   workup.STIRRINGThe solution was kept stirring at 0° C. for 30 minutes
4. 4
   workup.ADDITIONadded drop-wise to the flask through the rubber septum
5. 5
   workup.WAITThe reaction mixture was left
6. 6
   workup.STIRRINGstirring under nitrogen
7. 7
   Temperaturto warm back to room temperature over 14 hours

Vorschrift

An oven dried 50 mL round bottom flask was prepared with a magnetic stirring bar, a rubber septum cover, and a nitrogen inlet. 6-hydroxycoumarin (1) (114 mg, 0.7 mmol) and 4 mL of anhydrous N,N-dimethylformamide (DMF) were added to the round bottom flask. The solution was stirred and cooled to 0° C. in a salt-ice bath. Sodium hydride (28 mg of 60% mineral oil suspension, 0.7 mmol) was added to the flask at which point the solution turned color from yellow to orange. The solution was kept stirring at 0° C. for 30 minutes. 1-Bromo-3,7-dimethyloctane (344.4 μL, 1.66 mmol) in 1 mL of DMF was cooled to 0° C. and added drop-wise to the flask through the rubber septum using a syringe. The reaction mixture was left stirring under nitrogen to warm back to room temperature over 14 hours. The desired product was obtained through preparatory thin layer chromatography using a 7:3 Hexanes:Ethyl acetate solvent system. The purified product was verified by NMR spectroscopy (1H-NMR, 13C-NMR) and high-resolution mass spectrometry (HRMS). 1H-NMR (300 MHz, CD3COCD3): δ 0.95-1.86 (19H), 4.08 (t, 2H), 6.40 (d, 1H, J=9 Hz), 7.17 (m, 2H), 7.27 (s, 1H), 7.92 (d, 1H, J=9 Hz); 13C-NMR (75 Hz, CD3COCD3): δ 19.91, 22.87, 22.97, 25.13, 25.37, 36.60, 37.92, 39.93, 67.54, 111.97, 117.58, 118.47, 120.28, 120.56, 129.10, 144.35, 149.19, 156.44, 160.77. FIRMS (EI) Calcd. for C19H26O3: 302.18820. found: 302.18871.

Quelle