Ethyl bromoacetate → Ethyl 2-(6-methoxynaphthalen-2-yl)acetate

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.

1. stirringthe mixture was stirred for 1 h
2. customThe layers were separated
3. extractionThe aqueous layer was extracted with EtOAc
4. washwashed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customevaporated
8. customto afford a crude material, which
9. washwas subjected to silica gel chromatography (gradient elution 0% to 20% EtOAc in hexanes)

ORD-Eintrag

ord-b71003e9bdeb4494a04d03a4eb2f327d

Quelldatensatz

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08623818B2