Hydrochloric Acid → HCID 58289840, compound

HRID 2191905Notes

Reaction equation

HRID 2191905 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16]C)=O)#[N:6].Cl>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(OCC)C>[C:5]12([CH2:2][CH2:1]1)[C:7]1[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:13][C:14](=[O:16])[NH:6]2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 1512623Methyl(2-cyanophenyl)acetateHCID 178418443HCID 178418443, compound

Product 1

HCID 58289840HCID 58289840, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A diethyl ether solution (38 mL) of 2 M ethylmagnesium bromide was dropwise added at room temperature to a diethyl ether (200 mL) solution of methyl 2-cyanophenylacetate (10 g) and titanium tetraisopropoxide (17.9 g), and stirred for 1 hour. Aqueous 1 N hydrochloric acid solution was added to the reaction liquid, and the organic layer was separated. The aqueous layer was extracted with chloroform, the organic layer was washed with saturated saline water, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure. The crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate) to give the entitled compound as a colorless solid (1.8 g).

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with chloroform
  3. washthe organic layer was washed with saturated saline water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customThe crude product was purified through basic silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-de5fab3f6f3944f9b75c08fc26c4f934
Source dataset
uspto-grants-2012_12
Patent number
US08329711B2

Reaction notes

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