Tetrahydrofuran → HCID 67069111, compound

HRID 909812Notes

Reaction equation

HRID 909812 reaction equation
O1CCCC1.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:13])[CH:12]=1.C([Mg]Cl)(C)C.[CH2:19]([O:21][C:22]1[CH:29]=[CH:28][C:25]([CH:26]=[O:27])=[CH:24][CH:23]=1)[CH3:20]>O>[Br:13][C:11]1[CH:12]=[C:7]([CH:26]([C:25]2[CH:28]=[CH:29][C:22]([O:21][CH2:19][CH3:20])=[CH:23][CH:24]=2)[OH:27])[CH:8]=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 248344-EthoxybenzaldehydeHCID 693693,5-DibromopyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 67069111HCID 67069111, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A tetrahydrofuran solution (25 mL) of 3,5-dibromo pyridine (5 g, 0.0211 mol) was added dropwise to a mixture of a tetrahydrofuran solution (21.1 mL) of 1M isopropyl magnesium chloride and tetrahydrofuran (10 mL) at 4° C. for 15 minutes. After stirred at room temperature for 2.5 hours, the reaction mixture was added with 4-ethoxybenzaldehyde (2.93 mL, 0.0211 mol) and stirred for further 1.5 hours. After the reaction mixture was added with water while cooled on ice and extracted with ethyl acetate, the organic phase was washed with brine and dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain (5-bromopyridine-3-yl)(4-ethoxyphenyl)methanol (5.0 g, 77%) as a yellow oily substance.

Workup

  1. stirringstirred for further 1.5 hours
  2. temperaturewhile cooled on ice
  3. extractionextracted with ethyl acetate
  4. washthe organic phase was washed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. customthe residue obtained
  8. customby evaporating the solvent under reduced pressure
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6cddb7de0ed74c4caa27a727fae93314
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

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