반응 #530080

반응 방정식

1,1'-(azodicarbonyl) dipiperidine

5-methyl-3-(2-trifluoromethylbenzyloxy)phenol

tri-n-butylphosphine

1,3-propanediol

→

title compound

수율 88.1%

3-[5-Methyl-3-(2-trifluoromethylbenzyloxy)phenoxy]propanol

수율 88.1%

용매

Hexane

tetrahydrofuran

반응 조건

후처리

1. 1
   기타the precipitates were removed by filtration
2. 2
   기타The filtrate was evaporated in vacuo
3. 3
   기타the residue was purified by flash column chromatography (2:1 hexane/ethyl acetate)

실험 절차

To a solution of 5-methyl-3-(2-trifluoromethylbenzyloxy)phenol (1.41 g, 5.0 mmol), as prepared in the preceding step, tri-n-butylphosphine (1.62 g, 8.0 mmol) and 1,3-propanediol (1.90 g, 25 rnmol) in anhydrous tetrahydrofuran (50 mL) was added 1,1'-(azodicarbonyl) dipiperidine (2.01 g, 8.0 mmol). The mixture was stirred at ambient temperature overnight. Hexane (100 mL) was added to the mixture and the precipitates were removed by filtration. The filtrate was evaporated in vacuo, and the residue was purified by flash column chromatography (2:1 hexane/ethyl acetate) to give the title compound as a colorless oil (1.50 g, 84%). 1H-NMR (300 MHz, CDCl3) δ 7.74 (d, J=7.8 Hz, 1 H), 7.69 (d, J=7.8 Hz, 1 H), 7.56 (t, J=7.6 Hz, 1 H), 7.41 (t, J=7.7 Hz, 1 H), 6.41 (s, 1 H), 6.37 (s, 2 H), 5.23 (s, 2 H), 4.08 (t, J=6.0 Hz, 2 H), 3.85 (t, J=6.0 Hz, 2 H), 2.29 (s, 3 H), 2.02 (t, J =6.0 Hz, 2 H), 1.76 (s, 1 H).

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