2-phenyl-but-3-yne-1,2-diol

Base Information

• Chemical Name: 2-phenyl-but-3-yne-1,2-diol
• CAS No.: 1040274-54-1
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.188
• Mol file: 1040274-54-1.mol

Synonyms:2-phenyl-but-3-yne-1,2-diol

Chemical Property of 2-phenyl-but-3-yne-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-phenyl-but-3-yne-1,2-diol

There total 4 articles about 2-phenyl-but-3-yne-1,2-diol 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: 74.0%

2-phenyl-4-trimethylsilanyl-but-3-yne-1,2-diol (1429938-88-4) → 2-phenyl-but-3-yne-1,2-diol (1040274-54-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.333333h;

DOI:10.1002/chem.201203800

Reference yield: 52.0%

1-phenyl-2-hydroxyethanone (582-24-1) + acetylenemagnesium bromide (4301-14-8) → 2-phenyl-but-3-yne-1,2-diol (1040274-54-1)

Guidance literature:

acetylenemagnesium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h;

1-phenyl-2-hydroxyethanone; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 0.5h;

With water; ammonium chloride; In tetrahydrofuran; hexane;

DOI:10.1021/ol901942t

Reference yield:

1-phenyl-2-hydroxyethanone (582-24-1) → 2-phenyl-but-3-yne-1,2-diol (1040274-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; lithium bromide / tetrahydrofuran; hexane / 0.5 h / -40 °C / Inert atmosphere

1.2: 2 h / -40 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h

With n-butyllithium; tetrabutyl ammonium fluoride; lithium bromide; In tetrahydrofuran; hexane;

DOI:10.1002/chem.201203800

upstream raw materials:

1-phenyl-2-hydroxyethanone

acetylenemagnesium bromide

2-phenyl-4-trimethylsilanyl-but-3-yne-1,2-diol

benzaldehyde

Downstream raw materials:

3-phenylfuran

(R)-2-phenyl-2-((4-(trifluoromethyl)phenyl)amino)but-3-yn-1-ol

Refernces

• 1、 Tian, Lan,Gong, Liang,Zhang, Xia. "Copper-Catalyzed Enantioselective Synthesis of β-Amino Alcohols Featuring Tetrasubstituted Tertiary Carbons". . p. 2055 - 2059. Retrieved 2018/04/19.
• 2、 Egi, Masahiro,Azechi, Kenji,Akai, Shuji. "Cationic gold(I)-mediated intramolecular cyclization of 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols: A practical route to furans and pyrroles". supporting information; experimental part. p. 5002 - 5005. Retrieved 2009/12/26.