Reaktion #47337

Reaktionsgleichung

potassium carbonate

5,6,7,8-tetrahydro-naphthalen-1-ol

ethyl-2-butynoate

→

3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester

Ausbeute 72.5%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAt this time, the reaction was cooled to 25° C.
2. 2
   EinengenAt this time, the reaction was concentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (200 mL)
4. 4
   Waschenwas washed with water (1×100 mL)
5. 5
   TrocknenThe organics were then dried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Waschenrinsed with ethyl acetate
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeabsorbed onto silica gel
10. 10
    SonstigePurification by Analogix flash chromatography (115 g, 1-10% ethyl acetate/hexanes)

Vorschrift

A mixture of 5,6,7,8-tetrahydro-naphthalen-1-ol (3.00 g, 20.24 mmol) and ethyl-2-butynoate (13.62 g, 121.46 mmol) in tetrahydrofuran (100 mL) was treated with potassium carbonate (3.10 g, 22.43 mmol) and 4-dimethylaminopyridine (0.26 g, 2.12 mmol). The reaction was then heated at 85° C. overnight. At this time, the reaction was cooled to 25° C. and was stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (200 mL) and was washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL). The organics were then dried over magnesium sulfate, filtered, rinsed with ethyl acetate and concentrated in vacuo. The material was taken up in ethyl acetate and absorbed onto silica gel. Purification by Analogix flash chromatography (115 g, 1-10% ethyl acetate/hexanes) afforded 3-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (3.82 g, 72%) as a light yellow oil: HR-ES-MS m/z calculated for C26H34N4O5 [M+H]+ 483.2602, observed 483.2603; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11 (t, J=7.1 Hz, 3H), 1.61-1.77 (m, 4H), 2.44 (s, 3H), 2.46 (br. s., 2H), 2.76 (br. s., 2H), 3.98 (q, J=7.1 Hz, 2H), 4.57 (s, 1H), 6.84 (d, J=7.7 Hz, 1H), 7.03 (d, J=7.7 Hz, 1H), 7.18 (t, J=7.7 Hz, 1H).

Quelle