ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate

Base Information

• Chemical Name: ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate
• CAS No.: 197725-99-8
• Molecular Formula: C₁₈H₂₈O₃Si
• Molecular Weight: 320.504
• Mol file: 197725-99-8.mol

Synonyms:

Chemical Property of ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate

There total 2 articles about ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate 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:

3-(tert-Butyldimethylsiloxymethyl)benzyl Alcohol (81805-53-0) → ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate (197725-99-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 min

2: 1.) NaH / 1.) THF, 25 deg C, 30 min, 2.) THF, 25 deg C, 1 h

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine;

DOI:10.1016/S0968-0896(97)00090-4

Reference yield:

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + 3-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde (81168-11-8) → ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate (197725-99-8)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, 25 deg C, 30 min, 2.) THF, 25 deg C, 1 h;

DOI:10.1016/S0968-0896(97)00090-4

Reference yield:

ethyl-3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(E)-propenoate (197725-99-8) → 5-hydroxy-6-[3-(3-hydroxy-1E,5Z-undecadienyl)phenyl]hexanoic acid

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) diisobutylaluminium hydride, 2.) MeOH, 3.) H₂O

2: 100 percent / DL-camphorsulfonic acid / CH₂Cl₂ / 1 h / 25 °C

3: 90 percent / aq. NaOH / ethanol / 2 h / Heating

4: 96 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: 55 percent / dimethylsulfoxide / 1 h / 60 °C

6: aq. NaOH / ethanol / 10 h / Heating

7: diethyl ether; ethyl acetate

8: 1.) n-BuLi, diisopropylamine / 1.) THF, -70 deg C, 1 h, 2.) THF, -70 deg C, 1 h

9: 90 percent / aq. hexamethylphosphoramide / 0.25 h / 190 °C

10: 100 percent / NaBH₄ / methanol / 0.25 h / 0 °C

11: 100 percent / pyridine / 1 h / 50 °C

12: 1.11 g / aq. AcOH / tetrahydrofuran / 1.5 h / 70 °C

13: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C, 5 min

14: 1.) t-BuLi, 2.) triisopropylborate

15: 95 percent / H₂, quinoline / 5percent Pd(2.7percent Pb)-CaCO₃ / ethanol / 0.5 h / 25 °C

16: 86 percent / aq. NaOH / methanol; tetrahydrofuran / 16 h / 25 °C

With pyridine; quinoline; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; Triisopropyl borate; camphor-10-sulfonic acid; water; hydrogen; tert.-butyl lithium; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; Pd(2.7 percent Pb)-CaCO₃; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0968-0896(97)00090-4

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

3-(((tert-butyldimethylsilyl)oxy)methyl)benzaldehyde

3-(tert-Butyldimethylsiloxymethyl)benzyl Alcohol

Downstream raw materials:

3-[3-(tert-butyldimethylsilyloxymethyl)phenyl]-(2E)-propenol

3-(3-tetrahydropyranyloxy-1E-propenyl)benzylalcohol

3-(3-tetrahydropyranyloxy-1E-propenyl)phenylacetonitrile

{3-[(E)-3-(Tetrahydro-pyran-2-yloxy)-propenyl]-phenyl}-acetic acid methyl ester