Ethanol → Ethyl 3-(fur-2-yl)-3-oxopropanoate

HRID 986233Notes

Reaction equation

HRID 986233 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[C:11]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)(=[O:13])[CH3:12].C(O)C>O1CCCC1>[O:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:11]([CH2:12][C:3]([O:7][CH2:8][CH3:9])=[O:10])=[O:13]

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 7766Diethyl CarbonateHCID 145052-AcetylfuranHCID 24758Sodium hydride

Product 1

HCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoateYield 60.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (4.4 grams) and 10.7 grams of diethyl carbonate are suspended in 60 ml of tetrahydrofuran and 10 grams of 2-acetylfuran is gradually added thereto by keeping the inner temperature at 40°to 50° C. A small amount of ethanol is added thereto, heated to reflux for three hours, and the reaction is made stopped by addition of 20 ml of ethanol. The mixture is poured into ice water, extracted with ether, the ether extracts are combined, washed with water, dried with anhydrous magnesium sulfate, and ether is evaporated therefrom. The resulting oil is purified by distilling in vacuo to give 10 grams of pale yellow oily product, b.p. 90° C./3 mmHg.

Workup

  1. customat 40°to 50° C
  2. temperatureheated
  3. temperatureto reflux for three hours
  4. extractionextracted with ether
  5. washwashed with water
  6. dry with materialdried with anhydrous magnesium sulfate, and ether
  7. customis evaporated
  8. customThe resulting oil is purified
  9. distillationby distilling in vacuo

Sources & evidence

ORD record
ord-e606460048d245b2bc910732040c4650
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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