HCID 21109924, compound → HCID 12533584, compound

HRID 1766175Notes

Reaction equation

HRID 1766175 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8].[H][H]>C(O)C.O1CCCC1.[Pt]>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 2

HCID 21109924HCID 21109924, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12533584HCID 12533584, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.2 g (0.023 mol) of (E)-4-(3-bromo-4-fluorophenyl)-4-oxo-2-butenoic acid in a mixture of 200 ml ethanol and 25 ml tetrahydrofuran was hydrogenated in the presence of 1.0 g of 10% platinum/charcoal at ambient temperature under a pressure of 50 psi until the uptake of hydrogen was complete. The residue remaining after the catalyst and solvent had been eliminated crystallised spontaneously and after being washed thoroughly with diisopropylether yielded 1.7 g (27% of theoretical) of colourless crystals, m.p. 108–110° C. and Rf 0.73 (El F).

Workup

  1. customhad been eliminated crystallised spontaneously
  2. washafter being washed thoroughly with diisopropylether
  3. customyielded 1.7 g (27% of theoretical) of colourless crystals, m.p. 108–110° C. and Rf 0.73 (El F)

Sources & evidence

ORD record
ord-0e190501673f4109af546987fc2f16c2
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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