تفاعل #733197

معادلة التفاعل

ethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthalenecarboxylate

Na2CO3

4-hydroxyphenyl boronic acid

→

title compound

المردود 92.0%

Ethyl 6-(4-hydroxyphenyl)-1-naphthalenecarboxylate

المردود 92.0%

المذيبات

water

EtOAc

ethylene glycol dimethyl ether

ظروف التفاعل

المعالجة

1. 1
   أخرىThe EtOAc layer was separated
2. 2
   غسيلwashed with brine
3. 3
   تجفيفdried over MgSO4
4. 4
   ترشيحfiltered
5. 5
   تركيزthe filtrate was concentrated
6. 6
   أخرىto give the crude product as oil
7. 7
   أخرىThe crude material was purified by flash chromatography over SiO2 with a Hex

الإجراء التجريبي

A solution of ethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1-naphthalenecarboxylate (0.3 g, 0.861 mmol), tetrakis(triphenylphosphine) palladium (0) (0.04 g, 0.0345 mmol), 2 M Na2CO3 (4 mL) and 4-hydroxyphenyl boronic acid (0.143 g, 1.03 mmol) in ethylene glycol dimethyl ether (5 mL) was heated at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature, diluted with water and EtOAc. The EtOAc layer was separated, washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the crude product as oil. The crude material was purified by flash chromatography over SiO2 with a Hex:EtOAc (0 to 50% EtOAc) gradient to afford 0.23 g (92%) of the title compound as an oil. 1H NMR (400 MHz, DMSO-d6): δ 9.63 (s, 1 H), 8.76 (d, J=9.0 Hz, 1 H), 8.20 (m, 2 H), 8.07 (d, J=7 Hz, 1H), 7.93 (m, 1 H), 7.66 (d, J =9 Hz, 2 H), 7.58 (t, J=8 Hz, 1 H), 6.88 (d, J=9 Hz, 2 H), 4.42-4.37 (m, 2 H), 1.37 (t, J =7 Hz, 3 H).

المصدر