Reaction #1473

Reaction equation

(5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acid

ethyl 6-bromo-naphthalenecarboxylate

sodium carbonate

toluene

→

title compound

Ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)-naphth-7-yl]naphth-2-oate

Solvents

MeOH

Conditions

Workup

1. 1
   workup.ADDITIONThe reaction was diluted with 2N Na2 CO3
2. 2
   Extractionextracted with CH2Cl2 (2×)
3. 3
   Washthe organic layer was washed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Otherto give an oil
7. 7
   OtherThe crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane)

Procedure

To a degassed solution of 722 mg (2.6 mmol) of ethyl 6-bromo-naphthalenecarboxylate in 6.0 mL of toluene, was added sequentially 90 mg (0.08 mmol) of tetrakis-triphenylphosphine palladium (O), 5.0 mL (10.0 mmol) of 2M sodium carbonate, and a solution of 1.018 g (3.1 mmol) of (5,6,7,8-tetrahydro-5,5-dimethyl-8-(t-butyldimethylsilyloxy)naphth-2-yl)boronic acid (Compound B14) in 3.0 mL of MeOH. The reaction was heated at 90° C. for 15 h. The reaction was diluted with 2N Na2 CO3, and extracted with CH2Cl2 (2×), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an oil. The crude product was purified flash chromatography (silica, 5% ethyl acetate in hexane) to afford the title compound as a white solid.

Source