Reaktion #51511

Reaktionsgleichung

methyl bromoacetate

6-hydroxy-2-naphthoic acid methyl ester

Cs2CO3

→

product

Ausbeute 85.0%

6-Methoxycarbonylmethoxy-2-naphthoic acid methyl ester

Ausbeute 85.0%

Lösungsmittel

EtOAc

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThis layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL)
2. 2
   Trocknendried (MgSO4)
3. 3
   EinengenAfter concentration
4. 4
   Sonstigethe residue was recrystallized from MeOH

Vorschrift

To a stirred solution of 6-hydroxy-2-naphthoic acid methyl ester (0.500 g, 2.47 mmol) in acetone (25 mL) at rt was added Cs2CO3 (0.886 g, 2.72 mmol) followed by methyl bromoacetate (0.257 mL, 2.72 mmol) dropwise. After 18 h at this temperature, it was diluted with EtOAc (200 mL). This layer was washed with 1 N HCl (20 mL), sat. aq. NaHCO3 (20 mL), and brine (20 mL) and then dried (MgSO4). After concentration, the residue was recrystallized from MeOH:H2O to afford the product (0.573 g, 85%) as a solid; 1H NMR (DMSO-d6) δ3.71 (s, 3H), 3.87 (s, 3H), 4.95 (s, 2H), 7.30 (dd, J=2.6, 8.9 Hz, 1H), 7.38 (d, J=2.4 Hz, 1H), 7.87 (d, J=8.7 Hz, 1H), 7.92 (dd, J=1.6, 8.6 Hz, 1H), 8.06 (d, J=9.1 Hz, 1H), 8.55 (s, 1H); mass spectrum [(+) ESI], m/z 275 (M+H)+.

Quelle