dimethyl 2-hydroxy-3-phenylpropanephosphonate

Base Information

• Chemical Name: dimethyl 2-hydroxy-3-phenylpropanephosphonate
• CAS No.: 115869-34-6
• Molecular Formula: C₁₁H₁₇O₄P
• Molecular Weight: 244.227
• Mol file: 115869-34-6.mol

Synonyms:

Chemical Property of dimethyl 2-hydroxy-3-phenylpropanephosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 2-hydroxy-3-phenylpropanephosphonate

There total 1 articles about dimethyl 2-hydroxy-3-phenylpropanephosphonate 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:

phenylacetaldehyde (122-78-1) + dimethyl methane phosphonate (756-79-6) → dimethyl 2-hydroxy-3-phenylpropanephosphonate (115869-34-6)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -65 deg C, 1 h, 2.) THF, -65 deg C, 1 h;

DOI:10.1055/s-1988-27474

Reference yield:

dimethyl 2-hydroxy-3-phenylpropanephosphonate (115869-34-6) → 1-Methyl-2-((E)-4-methyl-penta-1,3-dienyl)-3-phenyl-1H-quinolin-4-one (115869-49-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 30 min., 2.) -65 deg C then room temp.

2: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, 0 deg C, 45 min., 2.) THF, -78 deg C, 1 min.

3: 86 percent / NaH / 15-crown-5 / tetrahydrofuran / 0 deg C then room temp., 30 min.

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; 15-crown-5; In tetrahydrofuran;

DOI:10.1055/s-1988-27474

Reference yield:

dimethyl 2-hydroxy-3-phenylpropanephosphonate (115869-34-6) → dimethyl 2-oxo-3-phenylpropylphosphonate (52343-38-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1.) CH₂Cl₂, -65 deg C, 30 min., 2.) -65 deg C then room temp.;

DOI:10.1055/s-1988-27474

upstream raw materials:

phenylacetaldehyde

dimethyl methane phosphonate

Downstream raw materials:

dimethyl 2-oxo-3-phenylpropylphosphonate

1-Methyl-2-((E)-4-methyl-penta-1,3-dienyl)-3-phenyl-1H-quinolin-4-one

(1-Methyl-4-oxo-3-phenyl-1,4-dihydro-quinolin-2-ylmethyl)-phosphonic acid dimethyl ester

(1-Isopropyl-4-oxo-3-phenyl-1,4-dihydro-quinolin-2-ylmethyl)-phosphonic acid dimethyl ester

Refernces