Reaction #44783

Reaction equation

N-(2,2-dimethoxyethyl)-4-iodobenzamide

→

2-(4-iodophenyl)oxazole

Yield 82.4%

Solvents

Eaton's reagent

Conditions

Workup

1. 1
   Temperatureto cool
2. 2
   OtherThe brown solid was isolated by filtration
3. 3
   OtherPurification on silica gel eluting with dichloromethane

Procedure

A solution of N-(2,2-dimethoxyethyl)-4-iodobenzamide (10 g, 30 mmol) in Eaton's reagent (100 mL) was heated at 135° C. for 17 hours. The reaction was allowed to cool and poured into ice water. The brown solid was isolated by filtration. Purification on silica gel eluting with dichloromethane gave 6.7 g of 2-(4-iodophenyl)oxazole, 1H NMR (400 MHz, CDCl3) δ 7.79 (q, 4H), 7.72 (s, 1H), 7.27 (s, 1H).

Source