Triphenylphosphine → 3-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl ester

HRID 1920941Notes

Reaction equation

HRID 1920941 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[S:21][N: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[S: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 66599297(3-Butyl-5-methyl-isoxazol-4-yl)-methanolHCID 178498604HCID 178498604, compound

Product 1

HCID 674921853-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-isothiazole-5-carboxylic acid methyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-butyl-5-methyl-4-isoxazolyl-methanol (367 mg, 2.2 mmol) in THF (10 mL) was added 3-hydroxy-isothiazole-5-carboxylic acid methyl ester (345 mg, 2.2 mmol) and triphenylphosphine (622 mg, 2.4 mmol) at 0° C. under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 1.04 mL, 2.4 mmol) was added and the reaction mixture was stirred overnight at room temperature. Concentration and purification by chromatography (silica, heptane:ethyl acetate=9:1 to 0:1) afforded the title compound (518 mg, 77%) as a colourless liquid. MS: m/e=311.2 [M+H]+.

Workup

  1. concentrationConcentration and purification by chromatography (silica, heptane:ethyl acetate=9:1 to 0:1)

Sources & evidence

ORD record
ord-f06824159db24acaa8904f1b7d0c2429
Source dataset
uspto-grants-2012_05
Patent number
US08173652B2

Reaction notes

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