반응 #640631

반응 방정식

2-(3-Trifluoromethyl-5-fluoro-phenylamino)-non-8-enoic acid methyl ester

lithium hydroxide monohydrate

→

title compound

수율 90.0%

2-(3-trifluoromethyl-5-fluoro-phenylamino)-non-8-enoic acid

수율 90.0%

용매

tetrahydrofuran

water

반응 조건

후처리

1. 1
   기타the reaction
2. 2
   기타to remove most of the tetrahydrofuran
3. 3
   workup.ADDITIONthe obtained solution was diluted with 1.5M hydrochloric acid (40 mL)
4. 4
   추출The solution was extracted with dichloromethane (2×60 mL)
5. 5
   추출The organic extracted
6. 6
   건조dried over sodium sulfate
7. 7
   기타the solvent removed in vacuo

실험 절차

2-(3-Trifluoromethyl-5-fluoro-phenylamino)-non-8-enoic acid methyl ester (1.643 g, 4.73 mmol., 1 eq.) was dissolved in tetrahydrofuran (40 mL). A solution of lithium hydroxide monohydrate (0.596 g, 14.19 mmol., 3 eq.) in water (40 mL) was added dropwise and the reaction mixture stirred for a further 3 hours at ambient temperature by when LCMS analysis of an aliquot showed the reaction to be complete. The reaction mixture volume was reduced by half in vacuo to remove most of the tetrahydrofuran and the obtained solution was diluted with 1.5M hydrochloric acid (40 mL). The solution was extracted with dichloromethane (2×60 mL). The organic extracted were combined, dried over sodium sulfate and the solvent removed in vacuo to give 1.41 g (90%) of the title compound as a yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 6.68 (d, J=8.54 Hz, 1 H), 6.63 (s, 1 H), 6.44 (dd, J=1.98, 10.68 Hz, 1 H), 5.72-5.85 (m, J=6.64, 6.64, 10.28, 17.03 Hz, 1 H), 5.00 (dq, J=1.66, 17.15 Hz, 1 H), 4.95 (dt, J=0.97, 10.11 Hz, 1 H), 4.07 (dd, J=5.80, 6.87 Hz, 1 H), 2.19 (s, 2 H), 2.05 (q, J=6.87 Hz, 2 H), 1.90-1.99 (m, 1 H), 1.74-1.86 (m, 1 H), 1.43-1.51 (m, 2 H), 1.32-1.43 (m, 3 H). LC-MS: purity 98% (UV), tR 2.33 min, m/z [M+H]+334.10

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