反応 #1475

反応方程式

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

溶媒

methylene chloride

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   温度the reaction was warmed to 35° C. for one additional hour
3. 3
   抽出extracted with CH2Cl2 (2×)
4. 4
   洗浄The combined organic layer was washed with brine
5. 5
   乾燥dried over MgSO4
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to give an off

実験手順

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).

出典