HCID 54103280, compound → HCID 59205203, compound

HRID 2242142Notes

Reaction equation

HRID 2242142 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[CH:15]=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[OH:16][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:9]=1[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:8]

Participants

4

Reactant 2

HCID 54103280HCID 54103280, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 59205203HCID 59205203, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-benzoyl-pyridine-3-carbaldehyde (97 mg, ol) in THF (5 mL) at −78° C. was added 1.0 M phenylmagnesium bromide in THF (0.46 mL) and the reaction mixture stirred for 15 min. The reaction mixture was then quenched with aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by preparation TLC of silica gel with 10% methanol in dichloromethane to yield [3-(hydroxy-phenyl-methyl)-pyridin-4-yl]-phenyl-methanone as white crystals.

Workup

  1. customThe reaction mixture was then quenched with aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by preparation TLC of silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-dca07067f0ee44e29a62ef3aec7c48ba
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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