Hydrochloric Acid → Ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate

HRID 875081노트

반응식

HRID 875081 반응식
[CH2:1]([O:3][C:4]1[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH:9]=1)[CH3:2].[Li]N([Si](C)(C)C)[Si](C)(C)C.[CH2:21]([O:23][C:24](=[O:30])[C:25](OCC)=[O:26])[CH3:22].Cl>C(OCC)C.O1CCCC1.O.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[C:5](=[O:10])[CH:6]([C:25](=[O:26])[C:24]([O:23][CH2:21][CH3:22])=[O:30])[CH2:7][CH2:8][CH:9]=1)[CH3:2]

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 1215982-Ethoxycyclohex-2-en-1-oneHCID 178418261HCID 178418261, 화합물

생성물 1

HCID 44235432Ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate수율 76%

시약·촉매·용매 4

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

41.40 g (0.29 mol) of 2-ethoxycyclohex-2-en-1-one were dissolved in 310 mL of diethyl ether and 325 mL of 1M LiN(TMS)2 in tetrahydrofuran were added dropwise at −50° C. After 30 minutes at the same temperature, 44.2 mL of diethyloxalate were also added under stirring. The solution was kept at room temperature overnight (TLC chloroform). 300 mL of water were then added, the pH adjusted to 4-5 by adding 1 N HCl and the resulting solution extracted with ethyl acetate. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude was purified by chromatography on a silica gel column eluted by chloroform (76% yield as an oil).

후처리

  1. extractionthe resulting solution extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe crude was purified by chromatography on a silica gel column
  5. washeluted by chloroform (76% yield as an oil)

출처 및 근거

ORD 기록
ord-1659b6003398402c88a81deb3047172d
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981089B2

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