HCID 54103280, compound → HCID 59205190, compound

HRID 1712104Notes

Reaction equation

HRID 1712104 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.[CH3:17][Mg]Br>C1COCC1>[OH:16][CH:15]([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])[CH3:17]

Participants

4

Reactant 2

HCID 54103280HCID 54103280, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59205190HCID 59205190, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-benzoyl-pyridine-3-carbaldehyde (114 mg, 0.54 mmol) in THF (3 mL) at −78° C. was added 3.0 M methylmagnesium bromide in THF (0.27 mL) and the reaction mixture was 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 chromatography of silica gel with 5% methanol in dichloromethane to yield [3-(1-hydroxy-ethyl)-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 chromatography of silica gel with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-ebd27aa0864242e7a8f9bfc957f86353
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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