Glycidol → HCID 22607599, compound

HRID 2307829Notes

Reaction equation

HRID 2307829 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[O:9]1[CH2:11][CH:10]1[CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:12][CH:10]2[CH2:11][O:9]2)[CH:3]=1

Participants

6

Reactant 4

HCID 11164GlycidolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 22607599HCID 22607599, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-Bromo-pyridin-3-ol (0.50 g, 2.87 mmol), oxiranyl-methanol (0.38 mL, 5.74 mmol) and triphenylphosphine (1.50 g, 5.74 mmol) in anhydrous THF (20 mL) was added di-tert-butyl azodicarboxylate (DBAD) (1.32 g, 5.74 mmol) and the reaction mixture stirred at room temperature for 18 hrs and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10%-35% ethyl acetate/hexanes to provide the desire product (0.48 g, 73%).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash column chromatography on silica gel eluting with 10%-35% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-f323b91f989e4539a43802799f4d26eb
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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