2,6-Lutidine → HCID 19801961, compound

HRID 1646266Notes

Reaction equation

HRID 1646266 reaction equation
Cl[CH:2]([CH2:8][C:9]([Cl:12])([F:11])[F:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC1C=CC=C(C)N=1.[H][H]>O1CCCC1.[Pd]>[Cl:12][C:9]([F:10])([F:11])[CH2:8][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 3

HCID 79372,6-LutidineHCID 19801957Ethyl 2,4-dichloro-4,4-difluorobutanoateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 19801961HCID 19801961, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

22.1 g of ethyl 2,4-dichloro-4,4-difluorobutyrate are dissolved in 100 ml of absolute tetrahydrofuran. 10.7 g of 2,6-dimethylpyridine and 2.0 g of 5% palladium/carbon catalyst are added and then gaseous hydrogen is passed in under atmospheric pressure until the hydrogen uptake is 100% of theory. The catalyst is removed by filtration and the tetrahydrofuran is removed by distillation and then the remaining oil is poured onto water, and the organic phase is separated off, dried with sodium sulfate, filtered and distilled under atmospheric pressure. 14.0 g of ethyl 4-chloro-4,4-difluorobutyrate are obtained in the form of a colourless oil of boiling point 154°-156° C.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe tetrahydrofuran is removed by distillation
  3. additionthe remaining oil is poured onto water
  4. customthe organic phase is separated off
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. distillationdistilled under atmospheric pressure

Sources & evidence

ORD record
ord-089e2fad318f4f48b86301028e60cdc8
Source dataset
uspto-grants-1993_01
Patent number
US05179121

Reaction notes

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