(5-(Allyloxy)-6-chloro-4-vinylpyridin-2-yl)methanol → HCID 22313337, compound

HRID 965850Notes

Reaction equation

HRID 965850 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([CH:14]=[CH2:15])=[CH:7][C:8]([CH2:12][OH:13])=[N:9][C:10]=1[Cl:11])C=C>C1CCC([P+](C([P+](C2CCCCC2)(C2CCCCC2)C2CCCCC2)C2C=CC=CC=2)(C2CCCCC2)C2CCCCC2)CC1.Cl[Ru]Cl>[Cl:11][C:10]1[N:9]=[C:8]([CH2:12][OH:13])[CH:7]=[C:6]2[CH:14]=[CH:15][CH2:1][O:4][C:5]=12

Participants

3

Reactant 1

HCID 22313362(5-(Allyloxy)-6-chloro-4-vinylpyridin-2-yl)methanol

Product 1

HCID 22313337HCID 22313337, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 86306055bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichlorideCatalyst

Procedure

[5-(Allyloxy)-6-chloro-4-vinylpyridin-2-yl]methanol (225 mg, 1.0 mmol) is combined with bis (tricyclohexylphosphine) benzylidene ruthenium (IV) dichloride (16.5 mg, 0.02 mmol) in 5 ml CH2Ci2 and the reaction is stirred 4 h at RT. The volatiles are removed in vacuo and the residue is chromatographed over 15 g SiO2 (230-400 mesh) eluting with 40% EtOAc/hexane. The appropriate fractions are combined and concentrated to give 175 mg (89%) of (8-chloro-2H-pyrano[2,3-c]pyridin-6-yl)methanol as a tan solid. MS for C9H8ClNO2 (EI) m/z: 197 (M)+.

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is chromatographed over 15 g SiO2 (230-400 mesh)
  3. washeluting with 40% EtOAc/hexane
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-70e14927fd824002b04cafc0f1428e62
Source dataset
uspto-grants-2005_10
Patent number
US06951868B2

Reaction notes

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