反応 #63938

反応方程式

3,4-dihydro-7-hydroxy-1(2H)-naphthalenone

potassium tert-butoxide

naphthol

2-bromopropane

→

3,4-Dihydro-7-(1-methylethoxy)-1(2H)-naphthalenone

収率 65.0%

溶媒

dimethyl sulfoxide

dimethyl sulfoxide

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise over 45 minutes
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for an additional 45 minutes
3. 3
   workup.STIRRINGAfter stirring for an additional 30 hours
4. 4
   抽出extracted with dichloromethane (4×300 ml)
5. 5
   洗浄The combined organic layers were back-washed with water (2×150 ml)
6. 6
   乾燥dried (anhydrous magnesium sulfate)
7. 7
   その他evaporated (vacuum) to an oil residue
8. 8
   その他Flash chromatographic purification (silica gel, dichloromethane elution) of the residue
9. 9
   その他yielded 24.0 g (65% yield) of the analytically pure ether product as an oil

実験手順

A suspension of 24.3 g (0.22 mole) of potassium tert-butoxide in 240 ml of dimethyl sulfoxide under a nitrogen atmosphere was stirred and cooled in a cold water bath while a solution of 29.2 g (0.18 mole) of 3,4-dihydro-7-hydroxy-1(2H)-naphthalenone in 400 ml of dimethyl sulfoxide was added dropwise over 45 minutes. The mixture was stirred at room temperature for an additional 45 minutes, and then 23.7 ml (31.0 g; 0.25 mole) of 2-bromopropane was added in one portion. After stirring for an additional 30 hours, the mixture was added to 2.0 kg of ice/water and extracted with dichloromethane (4×300 ml). The combined organic layers were back-washed with water (2×150 ml), dried (anhydrous magnesium sulfate), and evaporated (vacuum) to an oil residue. Flash chromatographic purification (silica gel, dichloromethane elution) of the residue yielded 24.0 g (65% yield) of the analytically pure ether product as an oil, suitable for conversion to the naphthol described in Example 4.

出典