2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester

Base Information

• Chemical Name: 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester
• CAS No.: 337356-20-4
• Molecular Formula: C₂₆H₂₇NO₆
• Molecular Weight: 449.503

Synonyms:2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester

Chemical Property of 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester

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Technology Process of 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester

There total 3 articles about 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

acetyl chloride (75-36-5) + 2-{[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-hydroxy-methyl}-acrylic acid tert-butyl ester (337356-01-1) → 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester (337356-20-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 7h;

DOI:10.1055/s-2001-10815

Reference yield:

tert-Butyl acrylate (1663-39-4,25232-27-3) → 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester (337356-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DABCO / 0.5 h / 20 °C

2: pyridine; DCM / 2 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; 1: Baylis-Hillman reaction;

DOI:10.1016/S0968-0896(03)00105-6

Reference yield:

3-(4-benzyloxy-phenyl)-isoxazol-5-carbaldehyde (337355-81-4) → 2-{acetoxy-[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-methyl}-acrylic acid tert-butyl ester (337356-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DABCO / 0.5 h / 20 °C

2: pyridine; DCM / 2 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; 1: Baylis-Hillman reaction;

DOI:10.1016/S0968-0896(03)00105-6

upstream raw materials:

acetyl chloride

2-{[3-(4-benzyloxy-phenyl)-isoxazol-5-yl]-hydroxy-methyl}-acrylic acid tert-butyl ester

tert-Butyl acrylate

3-(4-benzyloxy-phenyl)-isoxazol-5-carbaldehyde

Downstream raw materials:

2-[1-[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-meth-(E)-ylidene]-5-oxo-hexanoic acid tert-butyl ester

2-[1-[3-(4-Benzyloxy-phenyl)-isoxazol-5-yl]-meth-(E)-ylidene]-5-oxo-hexanoic acid

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