2-(2-Hydroxyethyl)pyridine → HCID 117889087, compound

HRID 632515Notes

Reaction equation

HRID 632515 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:10][CH3:11])[CH:3]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH2:19]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([O:1][CH2:19][CH2:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 4

HCID 76752-(2-Hydroxyethyl)pyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5195414-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 117889087HCID 117889087, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirring ice-cooled mixture of 5.0 g of 4-hydroxy-2-methoxybenzaldehyde, 4.5 g of 2-(2-pyridyl)ethanol and 10.3 g of triphenylphosphine was added dropwise 15.8 g of a 40% solution of diethyl azodicarboxylate in toluene. The mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated, purified by silica gel column chromatography (hexane/acetone system) and further purified by silica gel column chromatography (hexane/AcOEt system) to give 5.84 g of the title compound (69% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel column chromatography (hexane/acetone system)
  3. customfurther purified by silica gel column chromatography (hexane/AcOEt system)

Sources & evidence

ORD record
ord-b016b3550c844f97a596ddd225742d1b
Source dataset
uspto-grants-2016_04
Patent number
US09321752B2

Reaction notes

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