2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol

Base Information

• Chemical Name: 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol
• CAS No.: 863782-58-5
• Molecular Formula: C₄₆H₇₀OSi₂
• Molecular Weight: 695.232
• Mol file: 863782-58-5.mol

Synonyms:2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol

Chemical Property of 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol

There total 9 articles about 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol 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-butyl-5-iodo-phenylethynyl)-triisopropyl-silane + 2-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol (863782-56-3) → 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol (863782-58-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1002/anie.200500484

Reference yield:

1-bromo-3-tert-butyl-5-[2-[tris(isopropyl)silyl]ethynyl]benzene (863782-50-7) → 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol (863782-58-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: t-BuLi / tetrahydrofuran / 0.08 h / -78 °C

1.2: ZnBr₂ / tetrahydrofuran / 0.5 h / -78 - 0 °C

1.3: 99 percent / Pd(Ph₃P)4 / tetrahydrofuran / 16 h / 20 °C

2.1: 79 percent / aq. HCl / tetrahydrofuran / 4 h / 20 °C

3.1: Ti(i-PrO)4; L-DIPT; 4 Angstroem molecular sieves / 2-methyl-propan-2-ol / 16 h / -50 - -20 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

5.1: K₂CO₃ / methanol / 1.5 h / 0 - 20 °C

6.1: L-selectride / tetrahydrofuran / 0.17 h / 0 °C

7.1: Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 16 h / 20 °C

With titanium(IV) isopropylate; hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; tert.-butyl lithium; L-Selectride; potassium carbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 3.1: Sharpless epoxidation / 4.1: Dess-Martin oxidation / 7.1: Sonogashira coupling;

DOI:10.1002/anie.200500484

Reference yield:

2-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-oxirane-2-carbaldehyde (863782-54-1) → 2,4-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol (863782-58-5)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 1.5 h / 0 - 20 °C

2: L-selectride / tetrahydrofuran / 0.17 h / 0 °C

3: Pd(PPh₃)2Cl₂; CuI; Et₃N / tetrahydrofuran / 16 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; L-Selectride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; 3: Sonogashira coupling;

DOI:10.1002/anie.200500484

upstream raw materials:

2-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-but-3-yn-2-ol

1-bromo-3-tert-butyl-5-[2-[tris(isopropyl)silyl]ethynyl]benzene

2-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-oxirane-2-carbaldehyde

2-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-prop-2-en-1-ol

Downstream raw materials:

acetic acid 1,3-bis-{3-tert-butyl-5-[(triisopropylsilanyl)-ethynyl]-phenyl}-1-methyl-prop-2-ynyl ester