Tetrahydrofuran → HCID 86684760, compound

HRID 1408892Notes

Reaction equation

HRID 1408892 reaction equation
C(C1[CH:5]=[C:6]([Cl:11])[C:7]([Cl:10])=[N:8][CH:9]=1)C=C.C[N+]1([O-])CC[O:16]CC1.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>O.[Os](=O)(=O)(=O)=O>[Cl:11][C:6]1[CH:5]=[C:22]([CH2:21][CH:20]([OH:16])[CH2:24][OH:23])[CH:9]=[N:8][C:7]=1[Cl:10]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 86684759HCID 86684759, compound

Product 1

HCID 86684760HCID 86684760, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×

Procedure

To a solution of 5-allyl-2,3-dichloropyridine 58 in THF (2 ml) and H2O (1 ml) was added NMO (280 mg, 2.393 mmol) and osmium tetraoxide (THF solution) (0.487 ml, 0.080 mmol) at 0° C. The mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with H2O, then extracted with EtOAc (3×10 mL). The organic layers were combined and washed with sat NaCl. The organic layer was dried over MgSO4, filtered and concentrated. The crude product was added to a silica gel chromatography column and was eluted with Hex/EtOAc 2:8. Collected fractions were evaporated to afford 59 (255 mg 1.148 mmol 72.0%) as a colorless oil.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washwashed with sat NaCl
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was added to a silica gel chromatography column
  7. washwas eluted with Hex/EtOAc 2:8
  8. customCollected fractions were evaporated

Sources & evidence

ORD record
ord-42d00e8621524c4296b98f9d1d371952
Source dataset
uspto-grants-2014_12
Patent number
US08921373B2

Reaction notes

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