반응 #52365

반응 방정식

[4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl] acetic acid methyl ester

Compound 27

[4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl] acetic acid methyl ester

sodium hydroxide

→

title compound

수율 82.0%

[4-(2,2,4,4-Tetramethyl-chroman-6-yl-ethynyl) phenyl] acetic acid

수율 82.0%

용매

methanol

반응 조건

후처리

1. 1
   workup.DISTILLATIONThe volatiles were distilled off in vacuo
2. 2
   추출extracted with ethyl acetate (×2)
3. 3
   세척The combined organic phase was washed with brine (×1)
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated in vacuo to a residue which
7. 7
   기타was purified by preparative reverse phase

실험 절차

A solution of [4-(2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl] acetic acid methyl ester (Compound 27, 0.047 g, 0.13 mmol) in 5 mL of methanol was treated with 1M sodium hydroxide solution (2 mL) and heated at 55° C. for 2 h. The volatiles were distilled off in vacuo and the residue was acidified with 10% hydrochloric acid and extracted with ethyl acetate (×2). The combined organic phase was washed with brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue which was purified by preparative reverse phase HPLC using 10% water in acetonitrile as the mobile phase to afford the title compound (0.034 g, 82%). 1H NMR (300 MHz, CDCl3): δ 7.49-7.45 (m, 3H), 7.26-7.22 (m, 3H), 6.75 (d, 1H, J=8.2 Hz), 3.65 (s, 2H), 1.84 (s, 2H), 1.36 (s, 6H), 1.35 (s, 6H).

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