Tetrahydrofuran → HCID 68502590, compound

HRID 1712096Notes

Reaction equation

HRID 1712096 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-49ab1115bb16472ea185b98a7fe1aaf2
Source dataset
uspto-grants-2010_09
Patent number
US07790895B2

Reaction notes

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