Réaction #51268

Équation de réaction

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

Solvants

water

ethyl ether

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture is degassed with nitrogen for 30 minutes
2. 2
   Autreis evaporated to dryness
3. 3
   Autrethe residue obtained
4. 4
   AutreThe organic phase is separated
5. 5
   Séchagedried over magnesium sulphate
6. 6
   Autreevaporated
7. 7
   AutreThe residue obtained
8. 8
   Autreis purified by chromatography on a silica column
9. 9
   Lavageeluted with a mixture
10. 10
    Autre2.85 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.

Mode opératoire

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.

Source