1,4-Dioxane → HCID 59205222, compound

HRID 2242137Notes

Reaction equation

HRID 2242137 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1[CH2:23][CH2:22][O:21][CH2:20]C1>C(OCC)(=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:9][CH2:8][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[C:7]1[CH:2]=[C:3]([CH:4]=[CH:23][C:22]=1[O:21][CH3:20])[CH:8]=[O:9]

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 111167404-Bromopyridine-3-carbaldehyde

Product 1

HCID 59205222HCID 59205222, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A flask was with charged 4-bromo-pyridine-3-carbaldehyde (376 mg, 2 mmol), 3-formal-6-methoxyphenelboronic acid (432 mg, 2.4 mmol), tetrakis(triphenylphosphine) palladium(0) (116 mg, 0.1 mmol), potassium phosphate (638 mg, 3 mmol) and 1,4-dioxane (20 mL). The reaction mixture was kept at 80° C. overnight, then diluted with ethyl acetate and washed with water then brine. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography to yield 3-(3-hydroxymethyl-pyridin-4-yl)-4-methoxy-benzaldehyde as a yellow oil.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-550be046e6764174844d2a17f8518196
Source dataset
uspto-grants-2010_03
Patent number
US07671065B2

Reaction notes

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