Ethyl 2-(triphenylphosphoranylidene)propionate → HCID 69057069, compound

HRID 860606Notes

Reaction equation

HRID 860606 reaction equation
[CH:1]([CH:4]1[C:8](=O)[O:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:5]1)([CH3:3])[CH3:2].[CH3:20][CH2:21][O:22][C:23]([C:25]([CH3:45])=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:24]>C1(C)C=CC=CC=1>[CH2:21]([O:22][C:23](=[O:24])[CH:25]([C:8]1[O:7][C:6]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:5][C:4]=1[CH:1]([CH3:3])[CH3:2])[CH3:45])[CH3:20]

Participants

4

Reactant 2

HCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 45123189HCID 45123189, compound

Product 1

HCID 69057069HCID 69057069, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Isopropyl-2-(4-trifluoromethyl-phenyl)-4H-oxazol-5-one (1.0 g, 3.69 mmol) and (carbethoxyethylidine)triphenyl-phosphorane (2.67 g, 7.37 mmol) are stirred in toluene (20 mL) at reflux 3 hr. The mixture is concentrated in vacuo and the residue is purified over silica eluting with 9:1 hexanes:ethyl acetate affording 2-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-propionic acid ethyl ester as a pale orange oil, 1.11 g, 85%. MS (M++1) 356.

Workup

  1. temperatureat reflux 3 hr
  2. concentrationThe mixture is concentrated in vacuo
  3. customthe residue is purified over silica eluting with 9:1 hexanes

Sources & evidence

ORD record
ord-21d9603856e74faf8c086d94b536978f
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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