2-Pyridinecarboxylic acid, 6-methoxy-4-(1-oxopropyl)-5-[(phenylmethoxy)methyl]-, propyl ester

Base Information

• Chemical Name: 2-Pyridinecarboxylic acid, 6-methoxy-4-(1-oxopropyl)-5-[(phenylmethoxy)methyl]-, propyl ester
• CAS No.: 183433-70-7
• Molecular Formula: C21H25NO5
• Molecular Weight: 371.433
• Mol file: 183433-70-7.mol

Synonyms:

Chemical Property of 2-Pyridinecarboxylic acid, 6-methoxy-4-(1-oxopropyl)-5-[(phenylmethoxy)methyl]-, propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pyridinecarboxylic acid, 6-methoxy-4-(1-oxopropyl)-5-[(phenylmethoxy)methyl]-, propyl ester

There total 9 articles about 2-Pyridinecarboxylic acid, 6-methoxy-4-(1-oxopropyl)-5-[(phenylmethoxy)methyl]-, propyl ester 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: 98.4%

5-Benzyloxymethyl-4-(2-ethyl-[1,3]dioxolan-2-yl)-6-methoxy-pyridine-2-carboxylic acid propyl ester (183433-68-3) → 5-Benzyloxymethyl-6-methoxy-4-propionyl-pyridine-2-carboxylic acid propyl ester (183433-70-7)

Guidance literature:

In water; trifluoroacetic acid; for 21h; Ambient temperature;

DOI:10.1021/jo970173f

Reference yield:

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 5-Benzyloxymethyl-6-methoxy-4-propionyl-pyridine-2-carboxylic acid propyl ester (183433-70-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / tetrahydrofuran / 1 h / 0 °C

2: 100 percent / TMSCl / 12 h / Ambient temperature

3: 89 percent / methanol / 20 h / Heating

4: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h

5: 71 percent / NaBH₄, n-Bu₄NCl / H₂O / 18 h

6: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C

7: 89 percent / Pd(OAc)2, K₂CO₃, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr

8: 98.4 percent / H₂O; trifluoroacetic acid / 21 h / Ambient temperature

With palladium diacetate; sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1021/jo970173f

Reference yield:

citrazinic acid (99-11-6) → 5-Benzyloxymethyl-6-methoxy-4-propionyl-pyridine-2-carboxylic acid propyl ester (183433-70-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 78 percent / POPCl₃, Me₄NCl / 2 h / 130 - 142 °C

2: 84 percent / tetrahydrofuran / 1 h / 0 °C

3: 100 percent / TMSCl / 12 h / Ambient temperature

4: 89 percent / methanol / 20 h / Heating

5: 1.) n-BuLi / 1.) heptane, hexane, 0 deg C, 30 min, 2.) hexane, heptane, -30 deg C - 0 deg C, 1 h

6: 71 percent / NaBH₄, n-Bu₄NCl / H₂O / 18 h

7: 99.3 percent / t-BuOK / tetrahydrofuran / 1 h / 20 - 30 °C

8: 89 percent / Pd(OAc)2, K₂CO₃, DPP / dimethylformamide / 16 h / 90 °C / 775.7 Torr

9: 98.4 percent / H₂O; trifluoroacetic acid / 21 h / Ambient temperature

With palladium diacetate; sodium tetrahydroborate; n-butyllithium; chloro-trimethyl-silane; POPCl₃; parathion; potassium tert-butylate; tetrabutyl-ammonium chloride; tetramethlyammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1021/jo970173f

upstream raw materials:

5-Benzyloxymethyl-4-(2-ethyl-[1,3]dioxolan-2-yl)-6-methoxy-pyridine-2-carboxylic acid propyl ester

citrazinic acid

2,6-dichloropyridine-4-carboxylic acid

1-(2,6-dichloropyridin-4-yl)propan-1-one

Downstream raw materials:

5-Benzyloxymethyl-6-methoxy-4-(1-methylene-propyl)-pyridine-2-carboxylic acid propyl ester

Refernces