Hydrochloric Acid → HCID 66862425, compound

HRID 2368632Notes

Reaction equation

HRID 2368632 reaction equation
[K].CC(C)([O-])C.O1CCOCCOCCOCCOCCOCC1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][CH:28]=1.C[O:39][C:40](=O)[CH:41]([O:43][CH3:44])[CH3:42].Cl>O1CCCC1>[OH:35][C:33]([C:30]1[CH:29]=[CH:28][C:27]([C:26]([F:36])([F:37])[F:25])=[CH:32][CH:31]=1)=[CH:34][C:40](=[O:39])[CH:41]([O:43][CH3:44])[CH3:42]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2855718-Crown-6HCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 86599Propanoic acid, 2-methoxy-, methyl esterHCID 50987170Potassium tertbutoxide

Product 1

HCID 66862425HCID 66862425, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

10.14 g Potassium-tert.-butoxide and 225 mg 1,4,7,10,13,16-hexaoxacyclooctadecan are dissolved in 80 ml tetrahydrofurane. Then a solution of 10.0 g 1-(4-Trifluoromethyl-phenyl)-ethanone in 40 ml of tetrahydrofurane and a solution of 12.6 g racemic 2-Methoxy-propionic acid methyl ester in 40 ml of tetrahydrofurane are simultaneously added dropwise. After completion of addition the mixture is heated for four hours to reflux, cooled to 0° C. and hydrolyzed by dropwise addition of 50 ml of a 4 M solution of hydrochloric acid. The residue is partitioned between water and ethylacetate and the phases are separated. The aqueous phase is twice extracted with ethylacetate and the combined organic phases are washed with brine. After drying with magnesium sulphate the solvents are evaporated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 85:15).

Workup

  1. additionAfter completion of addition the mixture
  2. temperatureis heated for four hours
  3. temperatureto reflux
  4. customThe residue is partitioned between water and ethylacetate
  5. customthe phases are separated
  6. extractionThe aqueous phase is twice extracted with ethylacetate
  7. washthe combined organic phases are washed with brine
  8. dry with materialAfter drying with magnesium sulphate the solvents
  9. customare evaporated in vacuo
  10. customThe residue is chromatographed on silica gel (cyclohexane/ethylacetate 95:5 to 85:15)

Sources & evidence

ORD record
ord-d1dac388a28141df8c04d3328711df17
Source dataset
uspto-grants-2014_04
Patent number
US08703793B2

Reaction notes

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