Diethyl Ether → HCID 68193308, compound

HRID 1626797Notes

Reaction equation

HRID 1626797 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C[Li].[CH2:18](OCC)C.[Cl-].[NH4+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][C:11]([CH:12]([OH:13])[CH3:18])=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 19867320HCID 19867320, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68193308HCID 68193308, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Bromophenyl)nicotinaldehyde (3.2 g, 12 mmol) was dissolved in tetrahydrofuran (50 mL), and a solution of methyllithium in diethyl ether (1.0 M, 15 mL, 15 mmol) was added dropwise at −78° C. under a nitrogen atmosphere, followed by stirring at the same temperature for 1 hour. A saturated aqueous ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate, and subsequently the organic layer was concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure to afford 1-[6-(4-bromophenyl)pyridin-3-yl]ethanol (2.0 g, 7.2 mmol) as a white solid (yield 59%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationsubsequently the organic layer was concentrated under reduced pressure
  3. customThe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  4. concentrationa fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=2/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c4f3db619dd54b91b55e2aa3bdcd99c6
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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