Reacción #6582

Ecuación de reacción

2-(1-adamantyl)ethanol

diisopropylethylamine

1-acetyl-2-n-butyl 5-acetoxymethyl imidazole

triflic anhydride

→

5-acetoxymethyl-1-[2-(1-adamantyl)-ethyl]-2-n-butyl-imidazole

Disolventes

methanol chloroform

methylene chloride

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated
2. 2
   Temperaturaheated on a steam bath with 10% sodium hydroxide (250 ml)
3. 3
   workup.ADDITIONdiluted with 300 ml of water
4. 4
   Extracciónextracted with methylene chloride
5. 5
   Otrodried
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   Otroto give an oil

Procedimiento

A mixture of 2-(1-adamantyl)ethanol (10.7 g) and diisopropylethylamine (11 ml) in methylene chloride (70 ml) was added to triflic anhydride (16.75 g) in 70 ml of methylene chloride at -78° C. for 45 minutes, 1-acetyl-2-n-butyl 5-acetoxymethyl imidazole in 50 ml of methylene chloride was added and the mixture was allowed to stand at room temperature for 4 days, then concentrated and heated on a steam bath with 10% sodium hydroxide (250 ml), diluted with 300 ml of water, extracted with methylene chloride, dried, filtered and concentrated to give an oil. Chromatography on silica gel in methanol/chloroform gave 5-acetoxymethyl-1-[2-(1-adamantyl)-ethyl]-2-n-butyl-imidazole. This acetoxy compound (5.4 g) was stirred at room temperature with potassium hydroxide (5.2 g) in ethanol (200 ml) for one hour, the mixture was concentrated, poured into water, stirred, and filtered to give 1-[2-(1-adamantyl)ethyl]-2-n-butyl-5-hydroxymethyl- 1H-imidazole.

Fuente