Tetrahydrofuran → HCID 68502590, compound

HRID 2242136Notes

Reaction equation

HRID 2242136 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH2:8][OH:9].[CH2:10]([Li])[CH2:11][CH2:12][CH3:13].[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH:20]=[O:21])#[N:16].[CH2:25]1COC[CH2:26]1>>[OH:21][CH:20]([C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]([OH:9])[C:10]1[CH:26]=[CH:25][CH:13]=[CH:12][CH:11]=1)[C:19]1[CH:18]=[C:17]([CH:24]=[CH:23][CH:22]=1)[C:15]#[N:16]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 90670m-FormylbenzonitrileHCID 435086(4-bromopyridin-3-yl)methanolHCID 178418339Butyllithium

Product 1

HCID 68502590HCID 68502590, compound

Procedure

To a solution of (4-bromo-pyridin-3-yl)-methanol (53 mg 0.2 mmol) in THF (2 mL) at −78° C. was added dropwise 2.5 M n-butyllithium (0.24 mL, 0.6 mmol). After 15 min a solution of 3-cyanobenzaldehyde (79 mg) in THF (0.5 ml) was added. The reaction mixture was stirred for 15 min, then quenched with ammonium chloride solution and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated and the residue purified by flash chromatography to yield 3-{hydroxy-[3-(hydroxy-phenyl-methyl)-pyridin-4-yl]-methyl}-benzonitrile as white crystals.

Workup

  1. customquenched with ammonium chloride solution
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-189042e9d15b42d296c562f647b5cefb
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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