* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium hydroxide In tetrahydrofuran; water at 70℃; for 1 h;
Step 3: (0367) A 500 mL single-neck flask was charged with compound 14-c (20 g, 70.4 mmol), tetrahydrofuran (120 ml) and water (100 ml). 4N aqueous sodium hydroxide solution (40 ml) was added under stirring followed by stirring at 70° C. for 1 hour. The reaction mixture was extracted with ethyl acetate (70 ml×2), the pH of the aqueous phase was adjusted with concentrated hydrochloric acid to 12, the precipitated solid was filtered and dried to give compound 14-d (16 g, yield: 88percent).
Reference：
[1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1984, vol. 23, # 1, p. 38 - 41
[2] Patent: US2017/158680, 2017, A1, . Location in patent: Paragraph 0361; 0366; 0367
General procedure: 2,4-Dichloro-6-fluorobenzaldehyde (300.0 mg, 1.6 mmol), ethyl mercaptoacetate (204 uL,1.9 mmol), Et3N (556 uL, 4.0 mmol) and CH3CN (10 mL) were added into a 50 ml round bottom flask, and stirred at 60 C for overnight. The CH3CN was removed in vacuo, and the residue was dissolved in ethyl acetate (30 ml) and water (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2x). The combined organics were dried (MgSO4) and concentrated to give title compound (397.3 mg, 87%).
16
[ 360575-28-6 ]
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[ 93103-82-3 ]
Yield
Reaction Conditions
Operation in experiment
66%
With potassium carbonate; In N,N-dimethyl-formamide; at 60.0℃;Inert atmosphere;
Step 2: (0365) A three-necked flask was charged with N, N-dimethylformamide (250 ml) and potassium carbonate (51.5 g, 373 mmol). Ethyl thioglycolate (13.7 ml) was added dropwise at room temperature under a nitrogen atmosphere followed by rapid addition of compound 14-b (25.2 g, 124 mmol). The mixture was stirred at 60 C. overnight, diluted with ethyl acetate (300 ml), filtered, and the filtrate was washed with water and saturated brine, dried, concentrated and subjected to column chromatography to obtain compound 14-c (23 g, yield: 66%).
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