Reaktion #601232

Reaktionsgleichung

ethyl 2-(1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate

perchloric acid

→

oil

Ausbeute 105.0%

ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalen-2-yl)acetate

Ausbeute 105.0%

Lösungsmittel

tert-butylacetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with solid sodium bicarbonate, water (2 mL)
2. 2
   workup.ADDITIONadded
3. 3
   workup.STIRRINGstirred 1 hour
4. 4
   ExtraktionThe product was extracted with ethyl acetate
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Vorschrift

To a solution of ethyl 2-(1-(4-chlorophenyl)-6-methoxy-3-methylnaphthalen-2-yl)-2-hydroxyacetate (27 mg, 0.07 mmol) in tert-butylacetate (1.0 mL) was added 70% perchloric acid (0.012 mL, 0.14 mmol) and the reaction was stirred at room temperature for 1.5 hours. The reaction was quenched with solid sodium bicarbonate, water (2 mL) added and stirred 1 hour. The product was extracted with ethyl acetate, concentrated and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to give a colorless oil (16.2 mg). 1H-NMR: 400 MHz, (CDCl3) δ: 7.48 (s, 1H), 7.41-7.36 (m, 3H), 7.19 (d, J=6.4 Hz, 1H), 7.06 (d, J=9.2 Hz, 1H), 6.99 (br s, 1H), 6.86 (d, J=9.2 Hz, 1H), 5.00 (s, 1H), 4.12-4.02 (m, 2H), 3.82 (s, 3H), 2.52 (s, 3H), 1.13 (t, J=7.2 Hz, 3H), 0.91 (s, 9H).

Quelle