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Citation: WANG Ya-Lou, LIU Xing, LI Jiang-Chuan. Synthesis of 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol[J]. Chinese Journal of Applied Chemistry, ;2004, 21(1): 104-106. shu

Synthesis of 2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol

1.
Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009

Corresponding author: WANG Ya-Lou,
Received Date: 14 April 2003
Available Online: 17 June 2003

2-(5-Methyl-2-phenyl-4-oxazolyl)ethanol(1) was synthesized from L-aspartic acid via 5-step reactions; esterification, N-benzoylation, Dakin-West reaction, cyclizaction and reduction using LiAlH₄ in about 31.2% overall yield. Reacting L-aspartic acid with methanol in 0℃ gave 72.6% L-aspartic acid β-methyl ester hydrochloride(2), which was benzoylated to give 82.0% N-benzoyl-L-aspartic acid β-methyl ester(3). Dakin-West reaction of 3 gave 74.4% methyl 3-benzamido-4-oxovalerate(4), which was cyclized in toluene by POCl₃ to give 81.8% methyl 2-(5-methyl-2-phenyl-4-oxazolyl)acetate(5), the latter can easily convert to 1 by treatment with ether solution of LiAlH₄ in yield of 86%. All the compounds were characterized by ¹H NMR, IR and elemental analysis.
- (methyl-phenyl-oxazolyl)ethanol,
- Dakin-West reaction,
- reduction,
- synthesis
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