Triphenylphosphine → 3-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester

HRID 1920943Notes

Reaction equation

HRID 1920943 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([C:20]1[O:24][NH:23][C:22](=O)[CH:21]=1)=[O:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:16][O:17][C:18]([C:20]1[O:24][N:23]=[C:22]([O:14][CH2:13][C:12]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)=[N:9][O:10][C:11]=2[CH3:15])[CH:21]=1)=[O:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2724585Methyl 3-hydroxyisoxazole-5-carboxylateHCID 28473136(3-(4-Fluorophenyl)-5-methylisoxazol-4-yl)methanol

Product 1

HCID 674921743-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl esterYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (1.0 g, 4.8 mmol) in THF (70 mL) was added 3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (0.69 g, 4.8 mmol) and triphenylphosphine (1.65 g, 6.3 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (2.7 mL, 6.3 mmol) was added at 4° C. and the reaction mixture was stirred for 3 h at room temperature. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 7:3) afforded the title compound (958 mg, 60%) as a white solid. MS: m/e=333.2 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 7:3)

Sources & evidence

ORD record
ord-06998fba96424889aa4487902e73d5ce
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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