反应 #1472

反应方程式

ethyl acetate

ethyl 6-bromo-naphthalene-2-carboxylate

toluene

(5,6,7,8-tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid

→

title compound

Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-naphth-7-yl]naphth-2-oate

溶剂

hexane

sodium carbonate

MeOH

Na2CO3

反应条件

后处理

1. 1
   萃取extracted with CH2Cl2 (2×)
2. 2
   洗涤the organic layer was washed with brine
3. 3
   干燥dried over MgSO4
4. 4
   浓缩concentrated in vacuo
5. 5
   其他to give an oil

实验过程

To a degassed solution of 0.39 g (1.4 mmol) of ethyl 6-bromo-naphthalene-2-carboxylate and 3.0 mL of toluene, was added sequentially 49 mg (0.04 mmol) of tetrakis-triphenylphosphine palladium(0), 2.0 mL (2.0 mmol) of 1M sodium carbonate and then a solution of 0.32 g (1.6 mmol) of (5,6,7,8-tetrahydro-5,5-dimethylnaphth-2-yl)boronic acid (Compound B13) in 3.0 mL of MeOH. The reaction was heated at 80° C. for 6 h, diluted with 2N Na2CO3, and extracted with CH2Cl2 (2×), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. Flash chromatography (silica, 5% ethyl acetate in hexane) of the crude material gave the title compound as a white solid.

来源