Bn-OPT, Dudley Reagent

Base Information

• Chemical Name: Bn-OPT, Dudley Reagent
• CAS No.: 882980-43-0
• Molecular Formula: CF₃O₃S*C₁₃H₁₄NO
• Molecular Weight: 349.331
• Mol file: 882980-43-0.mol

Synonyms:2-Benzyloxy-1-methylpyridinium triflate;Bn-OPT, Dudley Reagent;2-Benzyloxy-1-methylpyridinium Trifluoromethanesulfonate;1-Methyl-2-(phenylmethoxy)-pyridinium 1,1,1-trifluoromethanesulfonate;Dudleys reagent;Bn-OPT

Chemical Property of Bn-OPT, Dudley Reagent

Chemical Property:

• Melting Point: 85-91 °C
• PSA: 78.69000
• LogP: 3.22230
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Benzyloxy-1-methylpyridinium triflate 96% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-37/38-41
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Dudley ReagentsNovel reagent for benzyl protection of alcohols under neutral conditions. Promotes selective formation of benzyl esters of carboxylic acids in presence of triethylamine.

Technology Process of Bn-OPT, Dudley Reagent

There total 5 articles about Bn-OPT, Dudley Reagent 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: 99.0%

2-benzyloxypyridine (40864-08-2) + methyl trifluoromethanesulfonate (333-27-7) → 2-benzyloxy-1-methylpyridinium triflate (882980-43-0)

Guidance literature:

In toluene; at 0 - 20 ℃; for 1h;

DOI:10.1055/s-0029-1219531

Reference yield:

2-chloropyridine (109-09-1) → 2-benzyloxy-1-methylpyridinium triflate (882980-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / KOH; 18-crown-6 / toluene / 1 h / Heating

2: 91 percent / toluene / 0.67 h / 20 °C

With potassium hydroxide; 18-crown-6 ether; In toluene;

DOI:10.1055/s-2005-921898

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → 2-benzyloxy-1-methylpyridinium triflate (882980-43-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / KOH; 18-crown-6 / toluene / 1 h / Heating

2: 91 percent / toluene / 0.67 h / 20 °C

With potassium hydroxide; 18-crown-6 ether; In toluene;

DOI:10.1055/s-2005-921898

upstream raw materials:

2-benzyloxypyridine

methyl trifluoromethanesulfonate

2-chloropyridine

benzyl alcohol

Downstream raw materials:

(2,6-dimethyloxy-4-methyl)phenyl

1-benzyl-2,4-dimethoxybenzene

1-benzyl-4-bromo-benzene

2-benzyl-1-bromobenzene

Refernces

• 1、 Albiniak, Philip A.,Dudley, Gregory B.. "New reagents for the synthesis of arylmethyl ethers and esters". scheme or table. p. 841 - 851. Retrieved 2010/07/10.
• 2、 Poon, Kevin W. C.,Albiniak, Philip A.,Dudley, Gregory B.,Berliner, Martin A.,Ragan, John A.. "Protection of alcohols using 2-benzyloxy-1-methylpyridinium trifluoromethanesulfonate: Methyl (R)-(–)-3-benzyloxy-2-methyl propanoate". . p. 295 - 305. Retrieved 2017/09/30.