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

HRID 875081ノート

反応式

HRID 875081 の反応式
[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]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 1215982-Ethoxycyclohex-2-en-1-oneHCID 178418261HCID 178418261、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1659b6003398402c88a81deb3047172d
出典データセット
uspto-grants-2015_03
特許番号
US08981089B2

反応ノート

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