Ethyl Acetate → HCID 18799859, compound

HRID 1637767Notes

Reaction equation

HRID 1637767 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6](I)[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1.[CH:13]([Sn](C=C)(C=C)C=C)=[CH2:14].C(OCC)(=O)C>CN(C)C=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([CH:13]=[CH2:14])[CH:5]=[C:4]([CH:10]([OH:12])[CH3:11])[N:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 66189TetravinylstannaneHCID 107092992-Chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine

Product 1

HCID 18799859HCID 18799859, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine (3.6 g, 12 mmol) in 36 mL of N,N-dimethylformamide is treated with bis(triphenylphosphine)-palladium dichloride (632 mg, 0.9 mmol) and tetravinyltin (2.7 mL, 15 mmol) and heated at 50° C. for 24 h and at room temperature for 40 h. The mixture is poured into 300 mL of ethyl acetate, filtered through a celite pad and the filtrate is washed with 4×50 mL of saturated sodium chloride. The organics are concentrated in vacuo and the crude material is chromatographed over 150 g of silica gel (230-400 mesh), eluting with 25% ethyl acetate/hexanes to provide 1.68 g (70%) of 2-chloro-3-hydroxy-4-vinyl-6-(1-hydroxyethyl)-pyridine.

Workup

  1. filtrationfiltered through a celite pad
  2. washthe filtrate is washed with 4×50 mL of saturated sodium chloride
  3. concentrationThe organics are concentrated in vacuo
  4. customthe crude material is chromatographed over 150 g of silica gel (230-400 mesh)
  5. washeluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-435c71bc7d3e44518e67d6e4f4da8325
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

Loading…