Tetrahydrofuran → HCID 59205184, compound

HRID 1712105Notes

Reaction equation

HRID 1712105 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.[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[CH3:19][O:20][C:21]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[CH:18][C:17]=1[CH:15]([OH:16])[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

3

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 54103280HCID 54103280, compound

Product 1

HCID 59205184HCID 59205184, compound

Procedure

To a solution of 4-benzoyl-pyridine-3-carbaldehyde (110 mg, 0.52 mmol) in THF (3 mL) at −78° C. was added 1.0 M 2,5-dimethoxymagnesium bromide in THF (1.04 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-[(2,5-dimethoxy-phenyl)-hydroxy-methyl]-pyridin-4-yl}-phenyl-methanone as a white solid.

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-886040872cda423485c023c9f9bb6b57
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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