Triphenylphosphine → 5-(2,2-difluorovinyl)2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine

HRID 464090Notes

Reaction equation

HRID 464090 reaction equation
[CH3:1][C:2]1([CH3:15])[O:14][C:6]2[C:7]([CH3:13])=[N:8][CH:9]=[C:10]([CH:11]=O)[C:5]=2[CH2:4][O:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:36]([F:41])([F:40])C([O-])=O.[Na+]>COCCOCCOC>[F:40][C:36]([F:41])=[CH:11][C:10]1[CH:9]=[N:8][C:7]([CH3:13])=[C:6]2[O:14][C:2]([CH3:15])([CH3:1])[O:3][CH2:4][C:5]=12

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2734985Sodium chlorodifluoroacetateHCID 156199462,2,8-trimethyl-4H-(1,3)dioxino(4,5-c)pyridine-5-carbaldehyde

Product 1

HCID 202639545-(2,2-difluorovinyl)2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A mixture of 0.1 mole of 2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine-5-carboxaldehyde, 0.11 mole of triphenylphosphine and 0.11 mole of sodium chlorodifluoroacetate in 100 ml. of diglyme is heated under nitrogen at 90° for 24hours. The reaction mixture is then filtered and concentrated in vacuo. Chromatography of the residue on silica gel and elution with etherpetroleum ether (10-50%) gives 5-(2,2-difluorovinyl)-2,2,8-trimethyl-4H-1,3-dioxino[4,5-c]pyridine.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated in vacuo
  3. washChromatography of the residue on silica gel and elution with etherpetroleum ether (10-50%)

Sources & evidence

ORD record
ord-01fb7e2310c64e979ca5e478bdd74128
Source dataset
uspto-grants-1985_10
Patent number
US04546106

Reaction notes

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