반응 #57423

ord-f6134be461a14511880bb3bc6c707851

반응 방정식

CC[O-].[Na+]
sodium ethoxide
CCOC(=O)C(=O)OCC
diethyl oxalate
CC(C)=O
acetone
[Na]
sodium
O=S(=O)(O)O
sulfuric acid
[Na]
sodium
CCOC(=O)C(O)=CC(C)=O
expected product
수율 101.0%
CCOC(=O)C(O)=CC(C)=O
Ethyl 2-hydroxy-4-oxopent-2-enoate
수율 101.0%

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타is prepared
  2. 2
    기타at ambient temperature
  3. 3
    기타has been completely consumed
  4. 4
    온도The reaction medium is maintained
  5. 5
    농축The reaction medium is subsequently concentrated under vacuum
  6. 6
    기타The crude reaction product
  7. 7
    기타is obtained
  8. 8
    추출The resulting aqueous phase is extracted with ethyl acetate (3×300 mL)
  9. 9
    건조dried over MgSO4
  10. 10
    농축concentrated under vacuum
  11. 11
    기타The crude reaction product
  12. 12
    기타is dried under vacuum
  13. 13
    기타to give

실험 절차

In a 2-liter three-neck round-bottom flask equipped with a dropping funnel and a paddle stirrer a solution of sodium ethoxide is prepared by reacting metallic sodium (7.74 g, 340.00 mmol, 1.2 eq) in anhydrous ethanol (800 ml) at ambient temperature until the metallic sodium has been completely consumed. A solution of diethyl oxalate (37.20 mL, 280.00 mmol, 1.0 eq) in acetone (10.30 mL, 280.00 mmol, 1.0 eq) is subsequently added dropwise at ambient temperature. The reaction medium is maintained with vigorous stirring for 2 hours. The reaction medium is subsequently concentrated under vacuum. The crude reaction product is diluted in water (200 ml). Ice (100 g) is added, followed by concentrated sulfuric acid (20 ml) in small portions, until a clear orange solution is obtained. The resulting aqueous phase is extracted with ethyl acetate (3×300 mL). The organic phases are combined, dried over MgSO4 and then concentrated under vacuum. The crude reaction product is dried under vacuum to give, quantitatively, the expected product (m=44.71 g).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07420087B2uspto-grants-2008_09