1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone

Base Information

• Chemical Name: 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone
• CAS No.: 186668-50-8
• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.343
• Mol file: 186668-50-8.mol

Synonyms:1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone

Chemical Property of 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone

There total 10 articles about 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone 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: 96.0%

3-benzyloxymethyl-4-(2-ethyl[1,3]dioxolan-2-yl)-2-methoxypyridine (880767-52-2) → 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone (186668-50-8)

Guidance literature:

With toluene-4-sulfonic acid; In ethanol; water; at 80 ℃; for 6.25h;

DOI:10.1021/jo060928v

Reference yield:

3-[(benzyloxy)methyl]-4-(2-ethyl-1,3-dioxolan-2-yl)-2-methoxypyridine (186668-49-5) + sodium hydrogencarbonate (144-55-8) → 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone (186668-50-8)

Guidance literature:

With trifluoroacetic acid; In water;

Reference yield:

4-(2-ethyl[1,3]dioxolan-2-yl)-2-methoxypyridine-3-carbaldehyde (880767-51-1) → 1-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-1-propanone (186668-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 88 percent / NaBH₄ / propan-2-ol; H₂O / 0.5 h / 0 °C

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

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

2.3: 96 percent / pyrrolidine / tetrahydrofuran / 3.5 h / 20 °C

3.1: 96 percent / PTSA*H₂O / ethanol; H₂O / 6.25 h / 80 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; water; isopropyl alcohol;

DOI:10.1021/jo060928v

upstream raw materials:

3-benzyloxymethyl-4-(2-ethyl[1,3]dioxolan-2-yl)-2-methoxypyridine

1-(2-methoxypyridin-4-yl)propan-1-one

2-chloro-4-pyridinenitrile

4-cyano-2-methoxypyridine

Downstream raw materials:

tert-butyl 3-{3-[(benzyloxy)methyl]-2-methoxy-4-pyridinyl}-3-hydroxypentanoate

(R)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid

(S)-3-(3-benzyloxymethyl-2-methoxypyridin-4-yl)-3-hydroxypentanoic acid