Réaction #1475

Équation de réaction

chloromethyl methyl ether

water

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

Hunig's base

t-butylammonium iodide

→

title compound

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

Solvants

methylene chloride

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   Températurethe reaction was warmed to 35° C. for one additional hour
3. 3
   Extractionextracted with CH2Cl2 (2×)
4. 4
   LavageThe combined organic layer was washed with brine
5. 5
   Séchagedried over MgSO4
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autreto give an off

Mode opératoire

To a cold (0° C.) solution of 130 mg (0.35 mmol) of ethyl-6-[5,6,7,8-tetrahydro-5,5-dimethyl-8-(hydroxy)-naphth-7-yl]naphth-2-oate (Compound B4) in 2.0 mL of methylene chloride was added 50 mg (0.15 mL, 0.86 mmol) of Hunig's base, followed by 0.21 g (0.20 mL, 2.6 mmol) chloromethyl methyl ether was added and stirred at room temperature for 14 h. About 500 mgs of t-butylammonium iodide was then added and the reaction was warmed to 35° C. for one additional hour. The reaction was diluted with water, and extracted with CH2Cl2 (2×). The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to give an off. The title compound was obtained as an oil after flash chromatography (silica, 10% ethyl acetate).

Source