2-Methoxy-4-propionylpyridine

Base Information

• Chemical Name: 2-Methoxy-4-propionylpyridine
• CAS No.: 880767-50-0
• Molecular Formula: C₉H₁₁NO₂
• Molecular Weight: 165.192
• DSSTox Substance ID: DTXSID40474882
• Wikidata: Q82305039
• Mol file: 880767-50-0.mol

Synonyms:2-Methoxy-4-propionylpyridine;880767-50-0;1-(2-methoxypyridin-4-yl)propan-1-one;1-Propanone, 1-(2-methoxy-4-pyridinyl)-;SCHEMBL2799836;DTXSID40474882;OBPIFCWDBWHHBE-UHFFFAOYSA-N;1-(2-methoxy-pyridin-4-yl)-propan-1-one;FT-0724697;N14282

Chemical Property of 2-Methoxy-4-propionylpyridine

Chemical Property:

• PSA: 39.19000
• LogP: 1.68290
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

98% ^*data from raw suppliers

1-(2-methoxy-4-pyridinyl)-1-Propanone 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(=O)C1=CC(=NC=C1)OC

Technology Process of 2-Methoxy-4-propionylpyridine

There total 2 articles about 2-Methoxy-4-propionylpyridine 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: 91.0%

4-cyano-2-methoxypyridine (72716-86-0) + ethylmagnesium chloride (2386-64-3) → 1-(2-methoxypyridin-4-yl)propan-1-one (880767-50-0)

Guidance literature:

4-cyano-2-methoxypyridine; ethylmagnesium chloride; In tetrahydrofuran; tert-butyl methyl ether; at 0 ℃; for 8.92h;

With water; In tetrahydrofuran; tert-butyl methyl ether; at 0 - 20 ℃; for 16h;

Reference yield:

2-chloro-4-pyridinenitrile (33252-30-1) → 1-(2-methoxypyridin-4-yl)propan-1-one (880767-50-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 23 h / 20 °C

2: TBME / tetrahydrofuran / 4.5 h / 0 °C

With tert-butyl methyl ether; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo060928v

Reference yield:

1-(2-methoxypyridin-4-yl)propan-1-one (880767-50-0) → (R)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid (220998-02-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 62 percent / H₂SO₄; para-toluenesulfonic acid monohydrate / toluene / 72 h / Heating

2.1: 2-bromomesitylene; n-BuLi / tetrahydrofuran; hexane / 3.5 h / -10 - 20 °C

2.2: 68 percent / tetrahydrofuran; hexane / -23 - 20 °C

3.1: 88 percent / NaBH₄ / propan-2-ol; H₂O / 0.5 h / 0 °C

4.1: LHMDS / tetrahydrofuran / 0.58 h / -78 - 20 °C

4.2: Bu₄NI / tetrahydrofuran / 16 h / 65 °C

4.3: 96 percent / pyrrolidine / tetrahydrofuran / 3.5 h / 20 °C

5.1: 96 percent / PTSA*H₂O / ethanol; H₂O / 6.25 h / 80 °C

6.1: LHMDS / tetrahydrofuran / 2 h / -78 °C

6.2: tetrahydrofuran / 1.25 h / -95 - -78 °C

6.3: aq. LiOH; aq. H₂O₂ / tetrahydrofuran / 1.5 h / 0 - 20 °C

With sodium tetrahydroborate; n-butyllithium; 2,4,6-trimethylphenyl bromide; sulfuric acid; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; water; isopropyl alcohol; toluene;

DOI:10.1021/jo060928v

upstream raw materials:

4-cyano-2-methoxypyridine

ethylmagnesium chloride

2-chloro-4-pyridinenitrile

Downstream raw materials:

(S)-5-Ethyl-5-hydroxy-2,5,6,9-tetrahydro-8-oxa-2-aza-benzocycloheptene-1,7-dione

Refernces

• 1、 Peters, Rene,Althaus, Martin,Diolez, Christian,Rolland, Alain,Manginot, Eric,Veyrat, Marc. "Practical formal total syntheses of the homocamptothecin derivative and anticancer agent diflomotecan via asymmetric acetate aldol additions to pyridine ketone substrates". . p. 7583 - 7595. Retrieved 2007/10/03.