반응 #483568

반응 방정식

CH3O2CCH(Cl)COCH2OCH3

thiobenzamide

→

title compound

수율 47.0%

4-Methoxymethyl-2-phenyl-thiazole-5-carboxylic Acid Methyl Ester

수율 47.0%

용매

EtOH

반응 조건

후처리

1. 1
   온도the resulting brown mixture refluxed under nitrogen for 8 hours
2. 2
   기타The mixture was partitioned between ethyl acetate and saturated NaHCO3
3. 3
   세척The organic layer was washed with water twice
4. 4
   건조brine, then dried over anhydrous sodium sulfate
5. 5
   농축concentrated in vacuo
6. 6
   기타to give a brown oil
7. 7
   세척Silica gel chromatography eluting with (9:1) hexanes-ethyl acetate

실험 절차

A solution of CH3O2CCH(Cl)COCH2OCH3 (68 mmole, 1.2 eq), prepared according to De Kimpe et al., Synthesis, 188 (1986), in absolute EtOH (75 ml) was treated with thiobenzamide (7.8 g, 56.7 mmole, 1.0 eq) and the resulting brown mixture refluxed under nitrogen for 8 hours. The mixture was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was washed with water twice and brine, then dried over anhydrous sodium sulfate and concentrated in vacuo to give a brown oil. Silica gel chromatography eluting with (9:1) hexanes-ethyl acetate provided 6.98 g (47%) of title compound as a yellow crystalline solid. 1H NMR (CDCl3): δ 3.6 (s, 3H), 3.9 (s, 3H), 4.95 (s, 2H), 7.4-7.5 (m, 3H), 8.0 (m, 2H).

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