Reaction #554629

Reaction equation

6-methoxynaphthalen-2-ylboronic acid

tri-o-tolylphosphine

K3PO4

ethylbromoacetate

→

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

Yield 76.3%

Solvents

THF

EtOAc

Water

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred for 1 h
2. 2
   OtherThe layers were separated
3. 3
   ExtractionThe aqueous layer was extracted with EtOAc
4. 4
   Washwashed with brine
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   Otherto afford a crude material, which
9. 9
   Washwas subjected to silica gel chromatography (gradient elution 0% to 20% EtOAc in hexanes)

Procedure

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.

Source