Triphenylphosphine → HCID 68884318, compound

HRID 1294305Notes

Reaction equation

HRID 1294305 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][OH:21])[O:17][N:16]=1.O[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][C:30]([O:32][CH3:33])=[O:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:19]=[C:18]([CH2:20][O:21][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][C:30]([O:32][CH3:33])=[O:31])[O:17][N:16]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178612053-(5-Methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol

Product 1

HCID 68884318HCID 68884318, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-(5 methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol (0.859 g), methyl 2-(2-hydroxyphenyl)acetate (0.499 g), triphenylphosphine (0.944 g) and tetrahydrofuran (15 mL) was dropwise added a solution (40%, 1.74 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography to give methyl 2-[2-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethoxy]phenyl]acetate as an oil from a fraction eluted with ethyl acetate-hexane (1:2, v/v). This oil was dissolved in methanol-tetrahydrofuran (1:1, 20 mL) and a 1N aqueous sodium hydroxide solution (10 mL) was added. The mixture was stirred at room temperature for 15 hrs. The reaction mixture was poured into water, 1N hydrochloric acid (10 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give crystals of 2-[2-[3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazoly]methoxylphenyl]acetic acid. Recrystallization from ethanol-hexane gave colorless needle crystals (0.651 g, 52%). melting point: 152-153° C.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3cd3f8749ac1432dacade5a95a959489
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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