Oxazole → 2,5-Diphenyloxazole

HRID 1848949Notes

Reaction equation

HRID 1848949 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1[CH:16]=[CH:15]N=C1>>[C:1]1([C:7]2[O:8][C:9]([C:16]3[CH:15]=[CH:3][CH:2]=[CH:1][CH:6]=3)=[CH:10][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 9255OxazoleHCID 5892802-Phenyl-1,3-oxazole

Product 1

HCID 71052,5-Diphenyloxazole

Procedure

FIG. 11 shows the molecular structures of the resultant molecule 2-phenyloxazole when the starting heterocycle is 1,3-oxazole, and its 1H NMR spectrum. 2,5-Diphenyloxazole is also produced in the synthesis. The synthesis of 2-phenyloxazole and 2,5-diphenyloxazole is conducted using copper(I) iodide (19.1 mg, 0.1 mmol), oxazole (69 mg, 1.0 mmol), iodobenzene (612 mg, 3.0 mmol), t-BuOLi (160 mg, 2.0 mmol), and DMF (1.0 mL). After column chromatography (hexanes, then 10% ethyl acetate in hexanes) and preparative HPLC (5% ethyl acetate in hexanes) 15 mg (7%) of a light tan solid (2,5-diphenyloxazole, Rf=0.30 (1/9 ethyl acetate/hexanes)) and 85 mg (59%) of a colorless oil (2-phenyloxazole, Rf=0.27 (1/9 ethyl acetate/hexanes)) are obtained. 1H NMR spectrum for 2-Phenyloxazole (300 MHz, CDCl3): δ7.23 (s, 1H), 7.42-7.49 (m, 3H), 7.71 (s, 1H), 8.01-8.10 (m, 2H). 1H NMR spectrum for 2,5-Diphenyloxazole (300 MHz, CDCl3): δ 7.31-7.38 (m, 1H), 7.40-7.52 (m, 6H), 7.70-7.75 (m, 2H), 8.08-8.15 (m, 2H). Table III, entry 1.

Sources & evidence

ORD record
ord-40a5f23ea83242d28335f99946aa9398
Source dataset
uspto-grants-2015_02
Patent number
US08952207B2

Reaction notes

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