Reaction #43374

Reaction equation

Water

sodium hydride

tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate

5-methyl-2-m-tolyloxazol-4-ylmethyl iodide

→

2-Methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid

Solvents

MTBE

Conditions

Workup

1. 1
   workup.ADDITIONthe solution is poured into a kieselguhr cartridge (VARIAN CHEM ELUT 1010)
2. 2
   WashThe product is eluted with MTBE
3. 3
   Concentrationconcentrated
4. 4
   workup.DISSOLUTIONThe residue is dissolved without purification in DCM/TFA (3:1)
5. 5
   workup.STIRRINGstirred at 40° C. for 5 h
6. 6
   ConcentrationThe solution is concentrated
7. 7
   Otherpurified by prep
8. 8
   OtherHPLC, resulting in 202 mg of 2-methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid

Procedure

200 mg of tert-butyl 2-(3-hydroxypropoxymethyl)-6-methylbenzoate are dissolved in 1.0 ml of MTBE, and 57 mg of sodium hydride (60% in mineral oil) are added. After gas evolution ceases, 446 mg of 5-methyl-2-m-tolyloxazol-4-ylmethyl iodide are added, and the suspension is stirred at RT overnight. Water is then added, and the solution is poured into a kieselguhr cartridge (VARIAN CHEM ELUT 1010). The product is eluted with MTBE and concentrated. The residue is dissolved without purification in DCM/TFA (3:1) and stirred at 40° C. for 5 h. The solution is concentrated and purified by prep. HPLC, resulting in 202 mg of 2-methyl-6-[3-(5-methyl-2-m-tolyloxazol-4-ylmethoxy)propoxymethyl]benzoic acid.

Source