(4-METHYL-2-PHENYL-1,3-OXAZOL-5-YL)METHANOL synthesis

5synthesis methods

Product Name:(4-METHYL-2-PHENYL-1,3-OXAZOL-5-YL)METHANOL
CAS Number:248924-06-3
Molecular formula:C11H11NO2
Molecular Weight:189.21

22260-83-9 Synthesis

METHYL 4-METHYL-2-PHENYL-1,3-OXAZOLE-5-CARBOXYLATE

22260-83-9
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(4-METHYL-2-PHENYL-1,3-OXAZOL-5-YL)METHANOL

248924-06-3
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Yield:248924-06-3 92%

Reaction Conditions:

with lithium aluminium tetrahydride in diethyl ether at 0; for 1 h;Inert atmosphere;

Steps:

1-10

The 4-Methyl-2-phenyloxazole-5-Methyl formate (215mg,1.0mmol) dissolved in anhydrous ether, The reaction system was cooled to 0 ° C, then LiAlH4 (57mg,1.5mmol) was added in portions, at 0 ° C reaction after 1 hour added ice water inactivated,The mixture was extracted twice with ethyl acetate and after the organic layer was washed with water and saturated brine, it was dried over anhydrous sodium sulfate and Concentration under reduced pressure to obtain the crude product.The compound was purified by column chromatography to obtain 4-Methyl-2-phenyloxazole-5-methanol(174mg,92%). The intermediate was taken with similar manner for the preparation of the compound LCZ-003, benzylbromide was replaced with p- Bromobenzyl bromide (350mg,1.4mmol), at last it was purified by column chromatography to obtain a product of 5 -((4-bromobenzyloxy) methyl) -4-methyl-2-phenyloxazole (268mg,83%).

References:

CN103694195,2016,B Location in patent:Paragraph 0269; 0271