Reaktion #1564460

Reaktionsgleichung

Sodium hydride

6-hydroxycoumarin

3,3-dimethylallyl bromide

→

desired product

6-((3-methylbut-2-en-1-yl)oxy)-2H-chromen-2-one

Lösungsmittel

N,N-dimethylformamide

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAn oven-dried 50 mL round bottom flask was prepared with a magnetic stirring bar
2. 2
   workup.STIRRINGthe solution was kept stirring at 0° C. for 30 minutes
3. 3
   workup.ADDITIONadded drop-wise to the flask through the rubber septum
4. 4
   workup.WAITThe reaction mixture was left
5. 5
   workup.STIRRINGstirring under nitrogen at room temperature for 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 and the solution was kept stirring at 0° C. for 30 minutes. 3,3-dimethylallyl bromide (192 μL, 1.66 mmol) in 1 mL of anhydrous 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 at room temperature for 14 hours. The desired product was isolated via column chromatography using a solvent system of 100% Hexanes, 20:1 Hexanes:Ethyl acetate, 15:1 Hexanes:Ethyl acetate, 10:1 Hexanes:Ethyl acetate, 7:3 Hexanes:Ethyl acetate, and 2:1 Hexanes:Ethyl acetate. The purified product was characterized by NMR spectroscopy (1H-NMR, 13C-NMR) and high-resolution mass spectrometry (HRMS). 1H-NMR (300 MHz, CDCl3): δ 1.76-1.87 (6H), 4.54 (d, 2H, J=6 Hz), 5.50 (m, 1H), 6.43 (m, 1H), 6.92-7.67 (4H); 13C-NMR (75 MHz, CDCl3): δ 18.68, 26.27, 65.86, 111.35, 117.42, 118.26, 119.44, 119.54, 120.53, 139.38, 143.69, 148.80, 155.71, 161.47. FIRMS (ES) Calcd. for C14H15O3: 231.1021. found: 231.1024.

Quelle