Ethyl Acetate → HCID 22038361, compound

HRID 1790454Notes

Reaction equation

HRID 1790454 reaction equation
[CH2:1]([Mg])[CH3:2].[F:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH:26]=[O:27])[CH:24]=4)[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[Cl-].[NH4+].C(OCC)(=O)C>CCOCC.O1CCCC1>[F:4][C:5]1[CH:29]=[CH:28][C:8]([CH2:9][CH2:10][N:11]2[CH2:12][CH2:13][CH:14]([N:17]3[C:25]4[C:20](=[CH:21][CH:22]=[C:23]([CH:26]([OH:27])[CH2:1][CH3:2])[CH:24]=4)[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 22038072HCID 22038072, compoundHCID 178461629HCID 178461629, compound

Product 1

HCID 22038361HCID 22038361, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 3 M solution (1.4 ml) of ethylmagnesium in ether was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-formylindoline (1.0 g) in tetrahydrofuran (30 ml) and the resultant mixture was allowed to warm to room temperature. Then a saturated aqueous solution of ammonium chloride and ethyl acetate were added to the reaction solution and the layers were separated. The organic layer was washed with brine and dried over magnesium sulfate. After removing the solvent, the residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (710 mg) as a colorless oil (yield: 66%).

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customAfter removing the solvent
  5. customthe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-f901dcfdd1f5429a82c4808f6b54f730
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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