Triphenylphosphine → 2-Methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1695379Notes

Reaction equation

HRID 1695379 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:13]=1[CH2:23]O.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:25])[N:7]=[C:8]([O:10][CH2:23][C:13]2[C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:15][O:16][C:12]=2[CH3:11])[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 1784986025-Hydroxy-1H-pyrazole-3-carboxylic acid methyl ester

Product 1

HCID 666438022-Methyl-5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-2H-pyrazole-3-carboxylic acid methyl esterYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-hydroxy-2H-pyrazole-3-carboxylic acid methyl ester (200 mg, 1.28 mmol) and (5-methyl-3-phenyl-4-isoxazolyl)methanol (260 mg, 1.37 mmol) in THF (10 mL) at 5° C. under argon was added triphenylphosphine (437 mg, 1.67 mmol), then diethyl azodicarboxylate (290 mg, 1.67 mmol) was added dropwise. The reaction mixture was warmed to room temperature for 3 h. The reaction mixture was then evaporated and purification by chromatography (silica, heptane:ethyl acetate=1:1 to 6.5:3.5) afforded the title compound (128 mg, 31%) as a colorless oil. MS: m/e=328.3 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurification by chromatography (silica, heptane:ethyl acetate=1:1 to 6.5:3.5)

Sources & evidence

ORD record
ord-ef8cac931afa4b079a0a1626a4fc0169
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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