1-Boc-5-benzyloxy-3-formylindole

Base Information

• Chemical Name: 1-Boc-5-benzyloxy-3-formylindole
• CAS No.: 914348-98-4
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.402
• Hs Code.: 2933990090
• Mol file: 914348-98-4.mol

Synonyms:1-Boc-5-Benzyloxy-3-formylindole;OR1674;

Chemical Property of 1-Boc-5-benzyloxy-3-formylindole

Chemical Property:

• Boiling Point: 511.7±58.0 °C(Predicted)
• PSA: 57.53000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 4.81600

Purity/Quality:

98%min ^*data from raw suppliers

1-Boc-5-benzyloxy-3-formylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Boc-5-benzyloxy-3-formylindole

There total 5 articles about 1-Boc-5-benzyloxy-3-formylindole 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: 50.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-benzyloxyindole-3-carboxaldehyde (6953-22-6) → tert-butyl 5-benzyloxy-3-formyl-1H-indole-1-carboxylate (914348-98-4)

Guidance literature:

5-benzyloxyindole-3-carboxaldehyde; With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 20 ℃; for 0.166667h;

di-tert-butyl dicarbonate; In dichloromethane; water; at 20 ℃; for 8h;

DOI:10.1055/s-0036-1588438

Reference yield:

5-benzyloxy-1H-indole (1215-59-4) → tert-butyl 5-benzyloxy-3-formyl-1H-indole-1-carboxylate (914348-98-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trichlorophosphate / 0.5 h / -30 - 20 °C

1.2: 1 h / 20 °C

2.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 0.17 h / 20 °C

2.2: 8 h / 20 °C

With tetrabutylammomium bromide; sodium hydroxide; trichlorophosphate; In dichloromethane; water; 1.1: |Vilsmeier-Haack Formylation / 1.2: |Vilsmeier-Haack Formylation;

DOI:10.1055/s-0036-1588438

Reference yield:

indol-5-ol (1953-54-4) → tert-butyl 5-benzyloxy-3-formyl-1H-indole-1-carboxylate (914348-98-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / Reflux

2.1: trichlorophosphate / 0.5 h / -30 - 20 °C

2.2: 1 h / 20 °C

3.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane; water / 0.17 h / 20 °C

3.2: 8 h / 20 °C

With tetrabutylammomium bromide; potassium carbonate; sodium hydroxide; trichlorophosphate; In dichloromethane; water; N,N-dimethyl-formamide; 2.1: |Vilsmeier-Haack Formylation / 2.2: |Vilsmeier-Haack Formylation;

DOI:10.1055/s-0036-1588438

upstream raw materials:

indol-5-ol

di-tert-butyl dicarbonate

5-benzyloxyindole-3-carboxaldehyde

5-benzyloxy-1H-indole

Refernces

• 1、 Abe, Takumi,Haruyama, Tomohiro,Yamada, Koji. "C4 Pictet-Spengler Reactions for the Synthesis of Core Structures in Hyrtiazepine Alkaloids". . p. 4141 - 4150. Retrieved 2017/09/13.