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

HRID 44573Notes

Reaction equation

HRID 44573 reaction equation
[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]

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 1N 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).

Workup

  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)

Sources & evidence

ORD record
ord-60daf26c88204986beac783c16ac945c
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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