Glycidol → HCID 21928118, compound

HRID 1243797Notes

Reaction equation

HRID 1243797 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:8]1[O:10][CH:9]1[CH2:11]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:10]1[CH2:8][CH:9]1[CH2:11][O:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11164GlycidolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418642HCID 178418642, compound

Product 1

HCID 21928118HCID 21928118, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask was added 4-hydroxypyridine (250 mg, 2.63 mmol), glycidol (194.74 mg, 2.63 mmol) and triphenylphosphine (758.45 mg, 2.89 mmol) in 20 mL of dry THF, followed by the addition of diethyl azodicarboxylate (503.6 mg, 2.89 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was diluted with CH2Cl2. The organic phase was washed with saturated NaHCO3 and brine. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. The residue was loaded to a flash chromatography column. The column was eluted with 0–5% MeOH/CH2Cl2. The product fractions were collected and concentrated to afford 80 mg (20.1%) of 4-oxiranylmethoxy-pyridine. (TLC: Rf=0.4, 5% MeOH/CH2Cl2, UV). MH+=152.31.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was diluted with CH2Cl2
  3. washThe organic phase was washed with saturated NaHCO3 and brine
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe column was eluted with 0–5% MeOH/CH2Cl2
  8. customThe product fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-313b2191e7014ba993c5425ebec0ce6d
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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