反应详情

A solution of 2-(2-methoxyethoxy)acetamide (Example 6A, 3.39 g, 25.5 mmol) in THF (40 mL) was treated with Lawesson's reagent (6.55 g, 16.19 mmol) and the reaction was refluxed for 18 hours. The reaction was then allowed to cool down to RT and was concentrated under vacuum, diluted with ethyl acetate, washed with sat. NaHCO3 (1×) and brine (1×). The aqueous phases were extracted with ethyl acetate (2×200 mL) and the organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (3.5×11 cm, 30% AcOEt/CH2Cl2) to give the title material (3.26 g, 86%) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.58 (very broad s, 1H), 7.50 (very broad s, 1H), 4.36 (s, 2H), 3.66-3.69 (m, 2H), 3.53-3.56 (m, 2H), 3.39 (s, 3H).

1. temperaturethe reaction was refluxed for 18 hours
2. concentrationwas concentrated under vacuum
3. additiondiluted with ethyl acetate
4. washwashed with sat. NaHCO3 (1×) and brine (1×)
5. extractionThe aqueous phases were extracted with ethyl acetate (2×200 mL)
6. dry with materialthe organic extracts were dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by silica gel chromatography (3.5×11 cm, 30% AcOEt/CH2Cl2)