Hydrochloric Acid → Ethyl 3-oxooxane-4-carboxylate

HRID 497487Notes

Reaction equation

HRID 497487 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][CH2:7][O:8][CH2:9][C:10](OCC)=[O:11])[CH3:2].CC(C)([O-])C.[K+].O1CCCC1.Cl>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH:5]1[CH2:6][CH2:7][O:8][CH2:9][C:10]1=[O:11])=[O:15])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21362494Ethyl 4-(2-ethoxy-2-oxoethoxy)butanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21362493Ethyl 3-oxooxane-4-carboxylateYield 48%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-ethoxycarbonylmethoxybutyric acid ethyl ester (90%, 15.0 g, 61.9 mmol) in toluene (300 mL) was stirred at room temperature and treated over 5 min with a solution of potassium tert-butoxide in tetrahydrofuran (1.0 M, 74.2 mL, 74.2 mmol). The mixture was stirred at room temperature for 24 h, then was poured into 1 N hydrochloric acid. The phases were separated, and the aqueous phase was extracted with ether. The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (5% ethyl acetate/hexanes) to provide the product as a pale yellow liquid (5.06 g, 48%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ether
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-56426b1e43bc442e9b8b98f15632c61a
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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