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

HRID 1455084Notes

Reaction equation

HRID 1455084 reaction equation
[CH2:1]([O:3][C:4]1[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH:9]=1)[CH3:2].[CH2:11]([O:13][C:14](=[O:20])[C:15](OCC)=[O:16])[CH3:12].C(Cl)(Cl)Cl.Cl>C(OCC)C.O1CCCC1.O>[CH2:1]([O:3][C:4]1[C:5](=[O:10])[CH:6]([C:15](=[O:16])[C:14]([O:13][CH2:11][CH3:12])=[O:20])[CH2:7][CH2:8][CH:9]=1)[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 7268Diethyl OxalateHCID 1215982-Ethoxycyclohex-2-en-1-one

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 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(1MS)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).

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-0827f59a73ab45eaa6c858d94cafd6e6
Source dataset
uspto-grants-2009_01
Patent number
US07482354B2

Reaction notes

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