반응 #59860

반응 방정식

methyl propionylacetate

triethyl orthoformate

1,3-dioxolan-2,2-diyldimethanol

sodium hydrogen carbonate

→

title compound

수율 35.8%

methyl(8-ethyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)acetate

수율 35.8%

용매

ethyl acetate

반응 조건

후처리

1. 1
   세척The organic layer was washed with water twice
2. 2
   건조with an aqueous saline solution, dried over anhydrous sodium sulfate
3. 3
   농축concentrated
4. 4
   기타The obtained crude product
5. 5
   기타was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-3/1-1/1 gradient)
6. 6
   농축a desired fraction(s) was concentrated

실험 절차

The 1,3-dioxolan-2,2-diyldimethanol (4 g, 29.8 mmol), which was obtained at another time in the same manner as described in the steps (4a)-(4c), was mixed with methyl propionylacetate (5.6 ml, 44.6 mmol) and triethyl orthoformate (5.2 ml, 31.3 mmol), and p-toluenesulfonic acid monohydrate (163 mg, 0.856 mmol). The mixture was stirred at room temperature for 3 hours. To the mixture, a saturated aqueous solution of sodium hydrogen carbonate and ethyl acetate were added. The organic layer was washed with water twice and with an aqueous saline solution, dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (elution solvent: heptane/ethyl acetate=1/0-3/1-1/1 gradient) and a desired fraction(s) was concentrated to obtain the title compound (2.63 g, yield: 35.8%) as a colorless oil.

출처