2-(2-Hydroxyethyl)pyridine → HCID 86708395, compound

HRID 402696Notes

Reaction equation

HRID 402696 reaction equation
[N+:1]([C:4]1[C:5]([CH3:11])=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH2:51][CH2:52]O>O1CCCC1>[CH3:11][C:5]1[CH:6]=[C:7]([O:10][CH2:52][CH2:51][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][N:45]=2)[CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 76752-(2-Hydroxyethyl)pyridineHCID 11776TriphenylphosphineHCID 174123-Methyl-4-nitrophenolHCID 75555Diisopropyl diazene-1,2-dicarboxylate

Product 1

HCID 86708395HCID 86708395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-nitro-m-cresol (3.0 g, 0.020 mmol) and triphenylphosphine (7.7 g, 0.029 mmol) in tetrahydrofuran (50 mL) cooled with ice bath, diisopropyl azodicarboxylate (5.8 mL, 0.030 mmol) was added dropwise. The mixture was stirred at ambient temperature for 30 min. The reaction mixture was cooled with ice bath, and a solution of 2-pyridineethanol (2.6 mL, 0.024 mmol) in tetrahydrofuran (5.0 mL) was added dropwise to the reaction mixture then the mixture was stirred at ambient temperature for further 16 h. The solvent was removed under reduced pressure, then the residue was purified by chromatography on silica gel(hexane/ethyl acetate) to afford 2-methyl-4-[2-(2-pyridinyl)ethoxy]-1-nitrobenzene as solid (2.0 g, y. 40%).

Workup

  1. temperatureThe reaction mixture was cooled with ice bath
  2. stirringthe mixture was stirred at ambient temperature for further 16 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by chromatography on silica gel(hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cee37e2d288642598e29f6cac9ae4c84
Source dataset
uspto-grants-2014_06
Patent number
US08742113B2

Reaction notes

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