Reaction #2912

Reaction equation

n-butyllithium

sodium hydrogen carbonate

trimethylsilylchloride

n-butyllithium

3-acetyl-2,5-dimethylfuran

4-Methylthiazole

→

title compound

1-(2,5-Dimethyl-3-furyl)-1-(4-methyl-5-thiazolyl)ethanol

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   TemperatureAfter 30 minutes the mixture was again cooled to -70° C.
3. 3
   Temperatureto warm to room temperature
4. 4
   workup.WAITAfter 30 minutes
5. 5
   Extractionthe mixture was extracted with diethylether
6. 6
   WashThe combined extracts were washed
7. 7
   Otherdried
8. 8
   Otherevaporated

Procedure

4-Methylthiazole (6.51 g) in dry tetrahydrofuran (50 ml) was stirred under an atmosphere of dry nitrogen and cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes trimethylsilylchloride (7.14 g) was added and the mixture was allowed to warm to room temperature. After 30 minutes the mixture was again cooled to -70° C. and n-butyllithium (2.5M solution in hexane, 29 ml) was added dropwise. After 30 minutes 3-acetyl-2,5-dimethylfuran (10 g) was added dropwise. The mixture was stirred at -70° C. for 1 hour and was then allowed to warm to room temperature. After 30 minutes, aqueous sodium hydrogen carbonate was added and the mixture was extracted with diethylether. The combined extracts were washed, dried and evaporated to give the title compound which was recrystallised from diethylether. M.p. 100.5°-101.5° C.

Source