Reaction #1152

Reaction equation

6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-methanol

→

6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-carbaldehyde

Yield 69.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   FiltrationAfter the insoluble portion was filtered off
2. 2
   Concentrationthe filtrate was concentrated
3. 3
   WashFrom the fraction eluted with ethyl acetate-chloroform (2:98

Procedure

A mixture of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-methanol (21.0 g), activated manganese dioxide (52.0 g) and tetrahydrofuran (800 ml) was stirred at 60° to 65° C. for 6 hours. After the insoluble portion was filtered off, the filtrate was concentrated; the residue was subjected to silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (2:98, v/v), crystals of 6-(5-methyl-2-phenyl-4-oxazolylmethoxy) benzofuran-2-carbaldehyde (14.3 g, 69%) were obtained, which was then recrystallized from dichloromethane-isopropyl propyl ether to yield colorless prisms having a melting point of 137° to 138° C.

Source