(5-tert-butyl-1,3-oxazol-2-yl)methanol synthesis

Yield:252662-39-8 100%

Reaction Conditions:

with sodium hydroxide;caesium carbonate;acetic acid in methanol;water;acetonitrile;

Steps:

5.A A.

A. Preparation of 2-hydroxymethyl-5-t-butyloxazole To a mixture of 2-chloromethyl-5-t-butyloxazole (13.0 g, 75.1 mmole), Cs₂CO₃ (36.0 g, 110.5 mmole) and acetic acid (10.5 mL, 192.6 mmole) in acetonitrile (120 ml) was heated at 65 deg C. overnight. All the solvent was removed under reduced pressure, the residue was partitioned between water (60 mL) and EtOAc (100 mL) and the aqueous layer was extracted with ethyl acetate (2*100 mL). The combined EtOAc solution was dried over MgSO₄ and concentrated to an oil. The oil was dissolved in methanol (30 mL) and added with a solution of NaOH (6.50 g, 163 mmole) in 30 ml of water, and stirred at room temperature overnight. MeOH was removed under reduced pressure, and the aqueous layer was extracted with EtOAc (3*80mL). The combined EtOAc solution was dried over MgSO₄ and concentrated to give 2-hydroxymethyl-5-t-butyloxazole as oil (11.76 g, 100%).

References:

US6407124,2002,B1