반응 #51268

반응 방정식

α-ethynyl-4,4-dimethylchroman-8-methanol

methyl 2-hydroxy-4-iodobenzoate

triethylamine

→

Methyl 2-hydroxy-4-[3-hydroxy-3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate

용매

water

ethyl ether

반응 조건

후처리

1. 1
   기타The reaction mixture is degassed with nitrogen for 30 minutes
2. 2
   기타is evaporated to dryness
3. 3
   기타the residue obtained
4. 4
   기타The organic phase is separated
5. 5
   건조dried over magnesium sulphate
6. 6
   기타evaporated
7. 7
   기타The residue obtained
8. 8
   기타is purified by chromatography on a silica column
9. 9
   세척eluted with a mixture
10. 10
    기타2.85 g (56%) of methyl 2-hydroxy-4-[3-hydroxy-3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate are collected in the form of a white solid with a melting point of 122-123° C.

실험 절차

3.00 g (13.9 mmol) of α-ethynyl-4,4-dimethylchroman-8-methanol, 3.90 g (13.9 mmol) of methyl 2-hydroxy-4-iodobenzoate and 100 ml of triethylamine are introduced into a three-necked flask. The reaction mixture is degassed with nitrogen for 30 minutes and then 780 mg (1.1 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 320 mg (1.7 mmol) of copper iodide are successively added. The reaction mixture is stirred at room temperature for 4 hours and is evaporated to dryness and the residue obtained is taken up in water and ethyl ether. The organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column eluted with a mixture composed of 50% ethyl acetate and 50% heptane. 2.85 g (56%) of methyl 2-hydroxy-4-[3-hydroxy-3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate are collected in the form of a white solid with a melting point of 122-123° C.

출처