반응 #51265

반응 방정식

3-(4,4-dimethylchroman-8-yl)-1-propyne

methyl 2-hydroxy-4-iodobenzoate

→

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

용매

triethylamine

반응 조건

후처리

1. 1
   기타The reaction mixture is degassed
2. 2
   workup.ADDITIONare introduced
3. 3
   기타The reaction mixture is evaporated to dryness
4. 4
   기타hydrochloric acid (1N), and the organic phase is separated
5. 5
   건조dried over magnesium sulphate
6. 6
   기타evaporated
7. 7
   기타The residue is purified by chromatography on a silica column
8. 8
   세척eluted with heptane
9. 9
   기타After evaporating the solvents
10. 10
    기타an oil, which slowly crystallizes
11. 11
    기타is obtained
12. 12
    기타is recrystallized from heptane
13. 13
    기타1.00 g (50%) of methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate is collected in the form of a white solid with a melting point of 92-93° C.

실험 절차

1.18 g (5.9 mmol) of 3-(4,4-dimethylchroman-8-yl)-1-propyne, 1.60 g (5.9 mmol) of methyl 2-hydroxy-4-iodobenzoate and 60 ml of triethylamine are introduced into a three-necked flask under argon. The reaction mixture is degassed by sparging with nitrogen, 332 mg (0.46 mmol) of bis(triphenylphosphine) palladium(II) chloride and 134 mg of copper iodide are introduced and the mixture is stirred at room temperature for eight hours. The reaction mixture is evaporated to dryness, the residue is taken up in ethyl acetate and hydrochloric acid (1N), and the organic phase is separated by settling, dried over magnesium sulphate and evaporated. The residue is purified by chromatography on a silica column eluted with heptane. After evaporating the solvents, an oil, which slowly crystallizes, is obtained and is recrystallized from heptane. 1.00 g (50%) of methyl 2-hydroxy-4-[3-(4,4-dimethylchroman-8-yl)prop-1-ynyl]benzoate is collected in the form of a white solid with a melting point of 92-93° C.

출처