(+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid

Base Information

• Chemical Name: (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid
• CAS No.: 1038432-31-3
• Molecular Formula: C₁₆H₂₃ClO₃Si
• Molecular Weight: 326.895
• Mol file: 1038432-31-3.mol

Synonyms:(+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid

Chemical Property of (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid

There total 1 articles about (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid 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: 100.0%

(±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate (1038432-24-4) → (+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid (1038432-31-3)

Guidance literature:

With lithium hydroxide; In acetonitrile; at 50 - 60 ℃;

DOI:10.1016/j.tetlet.2008.04.040

Reference yield:

(+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid (1038432-31-3) → bupropion (34841-39-9,34911-55-2,144445-75-0,144445-76-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / acetone / 0.08 h / 0 °C

2.1: sodium azide / acetone / 2 h / 20 °C

3.1: toluene / 2 h / Reflux; Inert atmosphere

4.1: water / 2 h / Reflux

5.1: sodium tetrahydroborate / methanol / 0.17 h / 0 - 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 30 h / 20 °C

8.1: 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride / dichloromethane / 0.5 h / -78 - -40 °C

8.2: 14 h / -40 - 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium azide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; water; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetone; toluene; 3.1: Curtius rearrangement;

DOI:10.1590/S0103-50532011000800022

Reference yield:

(+/-)-2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoic acid (1038432-31-3) + chloroformic acid ethyl ester (541-41-3) → C19H27ClO5Si

Guidance literature:

With triethylamine; In acetone; at 0 - 5 ℃; for 0.0833333h;

DOI:10.1016/j.tetlet.2008.04.040

upstream raw materials:

(±)-methyl 2-{[(tert-butyldimethylsilyl)oxy](3-chlorophenyl)methyl}prop-2-enoate

Downstream raw materials:

tert-butyl [2-(3-chlorophenyl)-2-tert-butyl-dimethyl-silanyloxy-1-(hydroxymethyl)ethyl]carbamate

C₁₄H₂₀ClNO₄

4-[hydroxy(3-chlorophenyl)methyl]-1,3-oxazolidin-2-one

(+/-)-1-[(tert-butyldimethylsilyl)oxy]-1-(3-chlorophenyl)propan-2-one