Triphenylphosphine → HCID 67491973, compound

HRID 1920922Notes

Reaction equation

HRID 1920922 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][OH:11])=[C:8]([CH3:12])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:13][O:14][C:15]([C:17]1[O:21][NH:20][C:19](=O)[CH:18]=1)=[O:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:13][O:14][C:15]([C:17]1[O:21][N:20]=[C:19]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:12])[CH:18]=1)=[O:16]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2724585Methyl 3-hydroxyisoxazole-5-carboxylateHCID 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanol

Product 1

HCID 67491973HCID 67491973, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-butyl-5-methyl-4-isoxazolyl-methanol (1.5 g, 8.9 mmol) in THF (30 mL) was added 3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (1.27 g, 8.9 mmol) and triphenylphosphine (2.79 g, 10.6 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 4.25 mL, 9.8 mmol) was added and the reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1) afforded the title compound (1.44 g, 55%) as a colourless liquid. MS: m/e=295.0 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, heptane:ethyl acetate=4:1 to 1:1)

Sources & evidence

ORD record
ord-470bf4b17c9841859c1da77e41f16449
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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