Methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate → Methyl 3-(4-(3-isopropyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

HRID 534857Notes

Reaction equation

HRID 534857 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[O:17][CH:18]=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[CH3:3]>C(O)C.[Pd]>[CH:2]([C:4]1[CH:5]=[C:6]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[O:17][CH:18]=2)[CH:7]=[C:8]([C:10]([F:12])([F:11])[F:13])[CH:9]=1)([CH3:3])[CH3:1]

Participants

4

Reactant 1

HCID 66750872Methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

Product 1

HCID 66750855Methyl 3-(4-(3-isopropyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a nitrogen sparged solution of methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 49, 0.200 g, 0.589 mmol) in ethanol (50.0 mL) was added 10% Pd/C (0.025 g) in a Parr bottle, and the mixture was vigorously shaken under an atmosphere of hydrogen (40 psi) at room temperature for 4 h. After this time, the reaction mixture was filtered through a pad of Celite, the filter cake was washed with ethanol and the filtrate was concentrated under reduced pressure to provide methyl 3-(4-(3-isopropyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.191 g, 95%) as a colorless oil.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with ethanol
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93bd1a53ff904bea9ff62b0482f477e5
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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