Triphenylphosphine → methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionate
Reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:37]=[CH:36][C:17]([CH2:18][N:19]2[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:20]2)=[CH:16][CH:15]=1.[CH3:38][C:39]1[O:40][C:41]([CH3:46])=[C:42]([CH2:44]O)[N:43]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:38][C:39]1[O:40][C:41]([CH3:46])=[C:42]([CH2:44][O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:18][N:19]3[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:21]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[N:20]3)=[CH:36][CH:37]=2)[N:43]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Diethyl azodicarboxylate (40% in toluene, 1.00 g) was added dropwise slowly to a mixture of methyl 3-[1-(4-hydroxybenzyl)-3-phenyl-1H-pyrazol-4-yl]propionate (500 mg), (2,5-dimethyl-4-oxazolyl]methanol (275 mg), triphenylphosphine (585 mg) and tetrahydrofuran (10 ml) at room temperature. After the mixture was stirred at room temperature for 8 hours, the reaction solvent was removed under reduced pressure. The residue was subjected to silica gel column chromatography, and methyl 3-[1-[4-(2,5-dimethyl-4-oxazolylmethoxy)benzyl]3-phenyl-1H-pyrazol-4-yl]propionate (288 mg, yield: 44%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (6:5, volume ratio).
Workup
- customthe reaction solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-285400df07fa4b3faee7b3ae4b351ae1
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179823B1
Reaction notes
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