反应 #805687

反应方程式

n-butyllithium

compound ( 87 )

2-ethoxy-1,8,9,9,10,10-hexafluoro-9,10-dihydrophenanthrene

acetic acid

hydrogen peroxide water

trimethyl borate

→

7-ethoxy-1,8,9,9,10,10-hexafluoro-9,10-dihydrophenanthrene-2-ol

收率 84.0%

溶剂

THF

反应条件

后处理

1. 1
   其他was returned to room temperature
2. 2
   其他The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride
3. 3
   萃取extracted with 50 mL of toluene three times
4. 4
   洗涤Combined organic layers were washed with a sodium thiosulfate aqueous solution
5. 5
   干燥a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate
6. 6
   workup.DISTILLATIONa solvent was distilled off by an evaporator
7. 7
   其他The residue was purified by silica gel column chromatography

实验过程

Under a nitrogen atmosphere, n-butyllithium (1.63 M, 8.71 mL, 14.20 mmol) was slowly added dropwise, at −60° C. or lower, to a THF (40 mL) solution of compound (87) (4.29 g, 12.91 mmol) prepared in Example 11. The reaction mixture was agitated at −60° C. or lower for 1 hour, and then trimethyl borate (1.61 g, 15.49 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then acetic acid (1.16 g, 19.37 mmol) and hydrogen peroxide water (2.93 g, 25.80 mmol) were added thereto, and the resultant mixture was agitated for 3 hours. The reaction mixture was quenched with a saturated aqueous solution of ammonium chloride, and extracted with 50 mL of toluene three times. Combined organic layers were washed with a sodium thiosulfate aqueous solution, a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was purified by silica gel column chromatography, and thus 7-ethoxy-1,8,9,9,10,10-hexafluoro-9,10-dihydrophenanthrene-2-ol (91) (3.76 g, yield 84.0%) was obtained.

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