反応 #486989

反応方程式

1-tri(n-butyl)stannyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzene

methyl 3-iodobenzoate

potassium fluoride

→

methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate

収率 14.4%

溶媒

dioxane

反応条件

後処理

1. 1
   温度was refluxed for 18 hours
2. 2
   ろ過Insoluble material was filtered
3. 3
   抽出was extracted with ethyl acetate (50 ml)
4. 4
   洗浄washed with brine
5. 5
   乾燥dried over magnesium sulfate
6. 6
   ろ過filtered
7. 7
   その他evaporated in vacuo
8. 8
   その他The residue was purified by column chromatography on silica gel (200 g) with benzene-ethyl acetate (20:1) as an eluent
9. 9
   workup.ADDITIONThe fractions containing the object compound
10. 10
    その他evaporated in vacuo
11. 11
    その他The residue was recrystallized from methanol

実験手順

A suspension of 1-tri(n-butyl)stannyl-2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)benzene (5 g), methyl 3-iodobenzoate (2.17 g) and tetrakis(triphenylphosphine) palladium(0) (0.29 g) in dioxane was refluxed for 18 hours. After being cooled to room temperature, 25% potassium fluoride aqueous solution (11 ml) was added to the reaction mixture and the mixture was stirred for 15 minutes. Insoluble material was filtered by using celite The filtrate was extracted with ethyl acetate (50 ml), washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography on silica gel (200 g) with benzene-ethyl acetate (20:1) as an eluent. The fractions containing the object compound were combined and evaporated in vacuo. The residue was recrystallized from methanol to afford methyl 3-[2-(4,4-dimethyl-4,5-dihydrooxazol-2-yl)phenyl]benzoate (370 mg).

出典