Triphenylphosphine → HCID 66643749, compound

HRID 1695409Notes

Reaction equation

HRID 1695409 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([OH:10])[CH:9]=1)=[O:4].[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[C:14]=1[CH2:24]O.C1(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]([CH3:11])[N:7]=[C:8]([O:10][CH2:24][C:14]2[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:16][O:17][C:13]=2[CH3:12])[CH:9]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 66643722(5-Methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanolHCID 178498598HCID 178498598, compound

Product 1

HCID 66643749HCID 66643749, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-hydroxy-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (355 mg, 2.28 mmol) and (5-methyl-3-pyridin-2-yl-isoxazol-4-yl)-methanol (432 mg, 2.28 mmol) in THF (10 mL) at 5° C. under argon was added triphenylphosphine (775 mg, 2.95 mmol), then diethyl azodicarboxylate (515 mg, 2.95 mmol) was added dropwise. The reaction mixture was warmed to room temperature overnight. Then the reaction mixture was evaporated and purified by chromatography (silica, heptane:ethyl acetate=1:1 to 7.5:2.5) to afford the title compound (220 mg, 30%) as a white solid. MS: m/e=329.3 [M+H]+.

Workup

  1. customThen the reaction mixture was evaporated
  2. custompurified by chromatography (silica, heptane:ethyl acetate=1:1 to 7.5:2.5)

Sources & evidence

ORD record
ord-6176fc202079455994dfca0d9101844a
Source dataset
uspto-grants-2012_04
Patent number
US08163728B2

Reaction notes

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