Reaction #1472

Reaction equation

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

Solvents

hexane

sodium carbonate

MeOH

Na2CO3

Conditions

Workup

1. 1
   Extractionextracted with CH2Cl2 (2×)
2. 2
   Washthe organic layer was washed with brine
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto give an oil

Procedure

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.

Source