(1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol

Base Information

• Chemical Name: (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol
• CAS No.: 1027287-47-3
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Mol file: 1027287-47-3.mol

Synonyms:(1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol

Chemical Property of (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol

There total 11 articles about (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol 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:

1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indole-4-carboxylic acid methyl ester (176963-44-3) → (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol (1027287-47-3)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - 20 ℃;

DOI:10.1016/0223-5234(96)89134-3

Reference yield:

5-methyl-2-methoxyphenol (1195-09-1) → (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol (1027287-47-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 57 percent / TiCl₄ / CH₂Cl₂ / 1 h / Ambient temperature

2: 61 percent / HNO₃, AcOH / tetrahydrofuran / 1 h / Ambient temperature

3: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 60 deg C, 1 h

4: 94 percent / NaH₂PO₄, NaClO₂ / H₂O; dimethylsulfoxide / 0.5 h / Ambient temperature

5: 88 percent / K₂CO₃ / dimethylformamide / 12 h / Ambient temperature

6: pyrrolidine / dimethylformamide / 6 h / Heating

7: 19 percent / Zn, 80percent aq. CH₃COOH / 85 °C

8: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min

9: H₂ / 10percent Pd/C / ethyl acetate; H₂O / 5 h / 760 Torr

10: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

11: diisobutylaluminium hydride / CH₂Cl₂; toluene / -78 - 20 °C

With pyrrolidine; sodium chlorite; sodium dihydrogenphosphate; hydrogen; nitric acid; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0223-5234(96)89134-3

Reference yield:

4-hydroxy-5-methoxy-2-methylbenzaldehyde (42044-81-5) → (1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-methanol (1027287-47-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 61 percent / HNO₃, AcOH / tetrahydrofuran / 1 h / Ambient temperature

2: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) DMF, 60 deg C, 1 h

3: 94 percent / NaH₂PO₄, NaClO₂ / H₂O; dimethylsulfoxide / 0.5 h / Ambient temperature

4: 88 percent / K₂CO₃ / dimethylformamide / 12 h / Ambient temperature

5: pyrrolidine / dimethylformamide / 6 h / Heating

6: 19 percent / Zn, 80percent aq. CH₃COOH / 85 °C

7: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min

8: H₂ / 10percent Pd/C / ethyl acetate; H₂O / 5 h / 760 Torr

9: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / Ambient temperature

10: diisobutylaluminium hydride / CH₂Cl₂; toluene / -78 - 20 °C

With pyrrolidine; sodium chlorite; sodium dihydrogenphosphate; hydrogen; nitric acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/0223-5234(96)89134-3

upstream raw materials:

1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indole-4-carboxylic acid methyl ester

5-methyl-2-methoxyphenol

4-hydroxy-5-methoxy-2-methylbenzaldehyde

4-hydroxy-5-methoxy-2-methyl-3-nitrobenzaldehyde

Downstream raw materials:

1-benzyl-6-methoxy-7-(methoxymethoxy)indole-4-carbaldehyde

(E)-3-(1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-2-methyl-acrylic acid

(E)-3-(1-Benzyl-6-methoxy-7-methoxymethoxy-1H-indol-4-yl)-2-methyl-acrylic acid ethyl ester

Refernces