Reaction #1474

Reaction equation

ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-7-yl]naphth-2-oate

ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-2-yl]naphth-2-oate

Compound B4

ethyl 6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-2-yl]naphth-2-oate

N-methylmorpholine N-oxide

ethyl acetate

→

title compound

Ethyl-6-[5,5-dimethyl-5,6-dihydro-naphthlen-8(7H)-one-2-yl]-naphthalen-2-oate

Solvents

water

methylene chloride

hexane

Conditions

Workup

1. 1
   Extractionextracted with CH2 Cl2 (2×)
2. 2
   WashThe combined organic layer was washed with brine
3. 3
   Dryingdried over MgSO4
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Otherto give a foam

Procedure

To a solution of 101 mg (0.27 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-hydroxy-naphth-7-yl]naphth-2-oate (Compound B4) in 1.5 mL of methylene chloride was added 50 mg (0.43 mmol) of N-methylmorpholine N-oxide and 6.0 mg (0.017 mmol) of tetrapropylammonium perruthenate(VII). The reaction was stirred at room temperature for 3 h, diluted with water, and extracted with CH2 Cl2 (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give a foam. The title compound was obtained as a white solid after flash chromatography (silica, 10% ethyl acetate in hexane).

Source