Pyridine → HCID 219358, compound

HRID 1350378Notes

Reaction equation

HRID 1350378 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH2:6]([OH:11])[CH:7]=[CH:8][CH2:9][OH:10].N1C=CC=CC=1>C1COCC1>[CH3:5][O:4][C:2](=[O:3])[O:10][CH2:9][CH:8]=[CH:7][CH2:6][O:11][C:2]([O:4][CH3:5])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 80652-Butene-1,4-diol

Product 1

HCID 219358HCID 219358, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine methyl chloroformate (7.04 g, 80.0 mmol) in THF (70 mL) and add dropwise to a ice-water cold solution of 2-buten-1,4-diol (majority Z form) (19.7 g, 208 mmol) and pyridine (16.5 g, 208 mmol) in THF (150 mL). Warm the mixture to room temperature and stir for 20 hours. Remove the pyridine salt by filtration and concentrate the filtrate to a residue. Dissolve the residue with CH2Cl2 and wash sequentially with 1 N HCl and brine. Dry the organic layer over Na2SO4 and concentrate the solvent in vacuo to give a residue. Purification by chromatography using hexanes: EtOAc=12:1 as the eluents give the title compound: 1H NMR (CDCl3): δ5.82–5.79 (m, 2H), 4.75 (d, J=4.8 Hz, 4H), 3.79 (s, 6H).

Workup

  1. customRemove the pyridine salt
  2. filtrationby filtration
  3. concentrationconcentrate the filtrate to a residue
  4. dissolutionDissolve the residue with CH2Cl2
  5. washwash sequentially with 1 N HCl and brine
  6. dry with materialDry the organic layer over Na2SO4
  7. concentrationconcentrate the solvent in vacuo
  8. customto give a residue
  9. customPurification by chromatography

Sources & evidence

ORD record
ord-f440bff8f6754a74b536ad58bfa49eba
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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