Acetate-hydrochloric acid → HCID 10443021, compound

HRID 1844083Notes

Reaction equation

HRID 1844083 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][C:6]1(C(OCC)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=2)[C:7]1=[O:16])C.Cl.C(O)(=O)C>>[F:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:16])[CH:6]([CH2:5][C:4]([OH:22])=[O:3])[CH2:14]2

Participants

3

Reactant 2

HCID 22641269Acetate-hydrochloric acidHCID 67973797HCID 67973797, compound

Product 1

HCID 10443021HCID 10443021, compoundYield 84.1%

Procedure

Ethyl 2-(2-ethoxy-2-oxo-ethyl)-5-fluoro-1-oxo-indane-2-carboxylate (500 mg, 1.6 mmol) was suspended in 1.4 ml mixture of 6 N HCl: acetic acid (1:1) and heated to reflux for 3 h. Reaction was monitored by TLC. Reaction mass was evaporated to dryness, 10 ml water was added and extracted with ethyl acetate (40 ml×3). Organic layer was washed with sat brine, dried over sodium sulphate. Crude product was washed with hexane to obtain a desired product (280 mg, 82%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h
  3. customReaction
  4. customReaction mass
  5. customwas evaporated to dryness, 10 ml water
  6. additionwas added
  7. extractionextracted with ethyl acetate (40 ml×3)
  8. washOrganic layer was washed with sat brine
  9. dry with materialdried over sodium sulphate
  10. washCrude product was washed with hexane

Sources & evidence

ORD record
ord-8909cabe15184ce8886da244c7c488cf
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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