Trimethylsilyldiazomethane → Methyl 2-(hydroxymethyl)-2'-methylbiphenyl-4-carboxylate

反応式

[CH3:1][Si](C=[N+]=[N-])(C)C.[OH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([OH:18])=[O:17])[CH:13]=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]>CO.C1(C)C=CC=CC=1>[OH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([O:18][CH3:1])=[O:17])[CH:13]=[CH:12][C:11]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25]

参加物

実験手順

(Trimethylsilyl)diazomethane (21 mL, 12.4 mmol) was added dropwise into a solution of 2-(hydroxymethyl)-2′-methylbiphenyl-4-carboxylic acid (2.0 g, 8.3 mmol) in MeOH (20 mL) and toluene (20 mL) at 0° C. After 10 minutes at 0° C., the resulting mixture was stirred at RT for 2 hours. The reaction mixture was concentrated under vacuum to give the title compound (2.1 g, quantitative), used without further purification in the next step. HPLC (Method A) Rt 3.95 min (purity 95.5%). 1H NMR (CDCl3, 300 MHz) δ 8.23 (d, J=1.3 Hz, 1H), 7.98 (dd, J=7.8, 1.9 Hz, 1H), 7.28-7.18 (m, 4H), 7.08 (d, J=7.3 Hz, 1H), 4.42 (d, J=5.7 Hz, 2H), 3.92 (s, 3H), 2.01 (s, 3H), 1.61 (t, J=5.7 Hz, 1H).