HCID 86750099, compound → HCID 23362243, compound

HRID 1082111Notes

Reaction equation

HRID 1082111 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[C:22](/[F:28])\[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[CH3:11]>C(O)C.[Pd]>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([F:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:16]=1)[CH3:11]

Participants

4

Reactant 1

HCID 86750099HCID 86750099, compound

Product 1

HCID 23362243HCID 23362243, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl (E)-3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-fluoropropenoate (3.79 g) in ethanol (80 mL) was hydrogenated over 10% Palladium-charcoal (0.74 g) at room temperature and pressure for 3 hrs. The mixture was filtered, concentrated in vacuo and the residue chromatographed twice on silica gel, firstly with 10% ethyl acetate in dichloromethane and then with 25% ethyl acetate in hexane as eluents to afford a gum. Crystallisation from ethyl acetate-hexane afforded the title compound, mp 65°-7° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue chromatographed twice on silica gel, firstly with 10% ethyl acetate in dichloromethane
  4. customwith 25% ethyl acetate in hexane as eluents to afford a gum
  5. customCrystallisation from ethyl acetate-hexane

Sources & evidence

ORD record
ord-2c8fa2b937bb49a395429c2aed9d109c
Source dataset
uspto-grants-1996_12
Patent number
US05589492

Reaction notes

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