3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole

Base Information

• Chemical Name: 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole
• CAS No.: 306775-20-2
• Molecular Formula: C₁₉H₂₆BNO₄S
• Molecular Weight: 375.297
• Mol file: 306775-20-2.mol

Synonyms:3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole

Chemical Property of 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole

There total 4 articles about 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole 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:

N-tosyl-N-allylpropargylamine (133886-40-5) → 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (306775-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / diethyl ether / -78 °C

1.2: diethyl ether

1.3: HCl / diethyl ether / -78 - 20 °C

2.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / 20 °C

With lithium diisopropyl amide; Grubbs catalyst first generation; In diethyl ether; dichloromethane;

DOI:10.1002/1521-3773(20000901)39:17<3101::AID-ANIE3101>3.0.CO;2-I

Reference yield:

N-allyl-N-(3-pinacolborylprop-2-yn-1-yl) toluenesulfonamide (306775-11-1) → 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (306775-20-2)

Guidance literature:

Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/1521-3773(20000901)39:17<3101::AID-ANIE3101>3.0.CO;2-I

Reference yield:

2-ethoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1126-93-8) → 3-[1-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-vinyl]-1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole (306775-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / diethyl ether / -78 °C

1.2: diethyl ether

1.3: HCl / diethyl ether / -78 - 20 °C

2.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / 20 °C

With lithium diisopropyl amide; Grubbs catalyst first generation; In diethyl ether; dichloromethane;

DOI:10.1002/1521-3773(20000901)39:17<3101::AID-ANIE3101>3.0.CO;2-I

upstream raw materials:

N-allyl-N-(3-pinacolborylprop-2-yn-1-yl) toluenesulfonamide

2-ethoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

N-tosyl-N-allylpropargylamine