反应 #554629

反应方程式

6-methoxynaphthalen-2-ylboronic acid

tri-o-tolylphosphine

K3PO4

ethylbromoacetate

→

ethyl 2-(6-methoxynaphthalen-2-yl)acetate

收率 76.3%

溶剂

THF

EtOAc

Water

反应条件

后处理

1. 1
   workup.STIRRINGthe mixture was stirred for 1 h
2. 2
   其他The layers were separated
3. 3
   萃取The aqueous layer was extracted with EtOAc
4. 4
   洗涤washed with brine
5. 5
   干燥dried over anhydrous sodium sulfate
6. 6
   过滤filtered
7. 7
   其他evaporated
8. 8
   其他to afford a crude material, which
9. 9
   洗涤was subjected to silica gel chromatography (gradient elution 0% to 20% EtOAc in hexanes)

实验过程

Into a 1 L round bottomed flask containing THF (335 mL) was added 6-methoxynaphthalen-2-ylboronic acid (20.15 g, 99.7 mmol, 1.2 eq), Pd(OAc)2 (563 mg, 2.51 mmol, 0.03 eq), tri-o-tolylphosphine (2.3 g, 7.56 mmol, 0.09 eq), K3PO4 (89 g, 419 mmol, 5 eq), and ethylbromoacetate (9.2 mL, 82.6 mmol, 1 eq). The resulting mixture was stirred for 24 h at room temperature. Water and EtOAc were added to the reaction and the mixture was stirred for 1 h. The layers were separated and both were saved. The aqueous layer was extracted with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude material, which was subjected to silica gel chromatography (gradient elution 0% to 20% EtOAc in hexanes) to afford ethyl 2-(6-methoxynaphthalen-2-yl)acetate (15.4 g, 76%) as a white, crystalline solid.

来源