1,1'-Carbonyldiimidazole → HCID 68288610, compound

HRID 541233Notes

Reaction equation

HRID 541233 reaction equation
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[CH:7]1[N:11]=[CH:10][N:9]([C:12](N2C=NC=C2)=[O:13])[CH:8]=1>O1CCCC1>[N:9]1([C:12]([O:6][C@@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[O:13])[CH:8]=[CH:7][N:11]=[CH:10]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 641512(-)-3-Hydroxytetrahydrofuran

Product 1

HCID 68288610HCID 68288610, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-tetrahydrofuran-3-ol (500 mg, 5.68 mmol, 1.00 equiv) and CDI (2 g, 12.33 mmol, 2.17 equiv) in tetrahydrofuran (50 mL) was stirred overnight under nitrogen at 60° C. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in 30 mL of DCM and washed with 1×50 mL of H2O. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:1) to yield 0.95 g (92%) of the title compound as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 30 mL of DCM
  3. washwashed with 1×50 mL of H2O
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-188263c412dc462e975584a386f996be
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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