4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene

Base Information

• Chemical Name: 4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene
• CAS No.: 319451-08-6
• Molecular Formula: C₁₂H₁₉NO₄Si
• Molecular Weight: 269.373
• Mol file: 319451-08-6.mol

Synonyms:4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene

Chemical Property of 4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

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Technology Process of 4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene

There total 1 articles about 4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene 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%

4-(methoxymethoxy)-1-nitrobenzene (880-03-5) + (trimethylsilyl)methylmagnesium chloride (13170-43-9) → 4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene (319451-08-6)

Guidance literature:

4-(methoxymethoxy)-1-nitrobenzene; (trimethylsilyl)methylmagnesium chloride; In tetrahydrofuran; diethyl ether; at -30 ℃; for 0.5h;

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; at -30 ℃; for 2h;

DOI:10.1248/cpb.54.163

Reference yield: 58.0%

4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene (319451-08-6) + 7-formyl-2-naphthalene-carbonitrile (179756-49-1) → 7-{1-hydroxy-2-[5-(methoxymethoxy)-2-nitrophenyl]ethyl}naphthalene-2-carbonitrile (319450-97-0)

Guidance literature:

4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene; 7-formyl-2-naphthalene-carbonitrile; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -10 ℃; for 0.5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1248/cpb.54.163

Reference yield:

4-(methoxymethoxy)-1-nitro-2-(trimethylsilylmethyl)benzene (319451-08-6) → (R)-7-{2-[2-amino-5-(methoxymethoxy)phenyl]-1-hydroxyethyl}naphthalene-2-carbonitrile (319451-70-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TBAF*H₂O / tetrahydrofuran / 0.5 h / -10 °C

1.2: 58 percent / aq. TBAF / tetrahydrofuran / 1 h / 20 °C

2.1: 76 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 4 h / 20 °C

3.1: 1.16 g / enantioselective HPLC separation on CHIRACEL OD column

With tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.54.163

upstream raw materials:

4-(methoxymethoxy)-1-nitrobenzene

(trimethylsilyl)methylmagnesium chloride

Downstream raw materials:

7-{1-hydroxy-2-[5-(methoxymethoxy)-2-nitrophenyl]ethyl}naphthalene-2-carbonitrile

(R)-7-{2-[2-amino-5-(methoxymethoxy)phenyl]-1-hydroxyethyl}naphthalene-2-carbonitrile

(S)-7-{2-[2-amino-5-(methoxymethoxy)phenyl]-1-hydroxyethyl}naphthalene-2-carbonitrile

7-{2-[2-amino-5-(methoxymethoxy)phenyl]-1-hydroxyethyl}naphthalene-2-carbonitrile